O-benzyloxime ethers and crop protection agents containing these compounds

ABSTRACT

O-Benzyloxime ethers of the formula I                    
     where 
     X is substituted or unsubstituted CH 2 , NOalkyl 
     Y is O, S, NR 5    
     R 1 , R 2 , R 5  are H, alkyl 
     Z 1 , Z 2  are H, halogen, methyl, methoxy, cyano 
     R 3 , R 4  are hydrogen, cyano, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, benzylthio, alkylcarbonyl, substituted or unsubstituted phenylcarbonyl, substituted or unsubstituted benzylcarbonyl, alkoxycarbonyl, substituted or unsubstituted phenoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl, 
     N(R 6 ) 2 , where R 6  is H, alkyl, substituted or unsubstituted phenyl, 
     —CO—N(R 7 ) 2 , where R 7  is H, substituted or unsubstituted alkyl, 
     substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted hetaryl, substituted or unsubstituted hetaryloxy, substituted or unsubstituted hetarylthio, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclyloxy, 
     R 3  and R 4  together may form a carbocyclic or heterocyclic ring which is substituted or unsubstituted, and 
     R 3  or R 4  may be halogen, or                    
      may be                    
      where 
     n is an integer from 1 to 4, and 
     R 8  is, or, when n&gt;1, the R 8 &#39;s are identical or different and are each, H, halogen, cyano, nitro or substituted or unsubstituted C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, aryl, aryloxy, benzyloxy, hetaryl or hetaryloxy. 
     and crop protection agents containing these compounds.

This application is a divisional of application Ser. No. 08/165,413,filed Dec. 13, 1993, now U.S. Pat. No. 5,387,607, which is a divisionalof application Ser. No. 07/962,340, filed Oct. 15, 1992, now U.S. Pat.No. 5,292,759, which is a divisional of application Ser. No. 07/722,209,filed Jun. 27, 1991, now U.S. Pat. No. 5,194,662.

The present invention relates to novel O-benzyloxime ethers and a methodfor controlling pests, in particular fungi, insects, nematodes andspider mites with these compounds.

It is known that substituted phenylacetic acid oxime derivatives can beused as fungicides (European Patent 253,213). However, their action isunsatisfactory.

We have found, surprisingly, that O-benzyloxime ethers of the generalformula I

where

X is CH₂, CH—C₁-C₄-alkyl, CH—C₁-C₄-alkoxy, CH—C₁-C₄-alkylthio orN—C₁-C₄-alkoxy,

Y is O, S or NR⁵,

R¹, R² and R⁵ are each H or C₁-C₄-alkyl,

Z¹ and Z² are identical or different and are each H, halogen, methyl,methoxy or cyano,

R³ and R⁴ are identical or different and are each hydrogen, cyano,straight-chain or branched C₁-C₁₀-alkyl, C₁-C₄-haloalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,arylthio-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₅-haloalkenyl,C₃-C₆-cycloalkenyl, C₃-C₆-halocycloalkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₄-alkylthio, benzylthio, C₁-C₄-alkylcarbonyl,unsubstituted or substituted phenylcarbonyl, unsubstituted orsubstituted benzylcarbonyl, C₁-C₄-alkoxycarbonyl, unsubstituted orsubstituted phenoxycarbonyl, unsubstituted or substitutedbenzyloxycarbonyl, unsubstituted or substituted aryl, unsubstituted orsubstituted aryloxy, unsubstituted or substituted arylthio,unsubstituted or substituted aryl-C₁-C₄-alkyl, unsubstituted orsubstituted aryl-C₁-C₄-alkenyl, unsubstituted or substitutedaryloxy-C₁-C₄-alkyl, unsubstituted or substituted arylthio-C₁-C₄-alkyl,unsubstituted or substituted hetaryl, unsubstituted or substitutedhetaryloxy, unsubstituted or substituted hetarylthio, unsubstituted orsubstituted hetaryl-C₁-C₄-alkyl, unsubstituted or substitutedhetaryl-C₂-C₄-alkenyl, unsubstituted or substitutedhetaryloxy-C₁-C₄-alkyl, unsubstituted or substituted heterocyclyl,unsubstituted or substituted heterocyclyloxy, N(R⁶)₂, where the radicalsR⁶ are identical or different and are each H, C₁-C₆-alkyl orunsubstituted or substituted phenyl, or

—CO—N(R⁷)₂, where the radicals R⁷ are identical or different and areeach H or C₁-C₄-alkyl, substituents, in addition to hydrogen, beinghalogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl,C₁-C₄-haloalkoxy, C₁-C₁₀-alkoximino-C₁- or C₂-alkyl, aryl, aryloxy,benzyloxy, hetaryl, hetaryloxy, C₃-C₆-cycloalkyl, heterocyclyl orheterocyclyloxy, or

R³ and R⁴ together may form a carbocyclic or heterocyclic ring which maybe substituted by the abovementioned substituents, and R³ or R⁴ may behalogen, or

 may be

 where

n is an integer from 1 to 4, and

R⁸ is, or, when n>1, the R⁸'s are identical or different and are each ,H, halogen, cyano, nitro or substituted or unsubstituted C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, aryl, aryloxy,benzyloxy, hetaryl or hetaryloxy,

have excellent fungicidal, insecticidal, nematicidal and acaricidalactivity which is better than that of the known phenylacetic acidderivetives.

The fungicidal action is preferred.

The radicals stated for the general formula I may, for example, have thefollowing meanings:

X may be C₁-C₄-alkylidene (eg. methylidene, ethylidene, n- orisopropylidene, n-, iso-, sec- or tert-butylidene),C₁-C₄-alkoxymethylidene (eg. methoxy-, ethoxy-, n-propoxy, isopropoxy-,n-butoxy-, isobutoxy-, sec-butoxy- or tert-butoxymethylidene),C₁-C₄-alkylthiomethylidene (eg. methyl-, ethyl-, n-propyl-, isopropyl-,n-butylthio-, isobutylthio-, sec-butylthio- ortert-butylthiomethylidene) or C₁-C₄-alkoximino (eg. methoximino,ethoximino, n-propoximino, isopropoximino, n-butoximino, isobutoximino,sec-butoximino or tert-butoximino),

Y may be O, S or NR⁵,

R¹, R² and R⁵ may each be H or C₁-C₄-alkyl (eg. methyl, ethyl, n- orisopropyl, n- or iso-, sec- or tert-butyl), Z¹ and Z² may be H, halogen(eg. fluorine, chlorine, bromine or iodine), methyl, methoxy or cyano,and

R³ and R⁴ may be identical or different and are each hydrogen, cyano,straight-chain or branched C₁-C₁₀-alkyl (eg. methyl, ethyl, n- orisopropyl, n-, iso-, sec- or tert-butyl, n-, iso-, sec-, tert- orneopentyl, n-hexyl or n-decyl), C₁-C₄-haloalkyl (eg. trifluoromethyl,2-fluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl,fluorodichloromethyl, difluorochloromethyl, chloromethyl,dichloromethyl, trichloromethyl, 2-chloroethyl, 2,2,2-trichloroethyl orpentachloroethyl), C₃-C₆-cycloalkyl (eg. cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl), C₃-C₆-halocycloalkyl (eg.2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl,2,2-dibromocyclopropyl, 2,2-dichloro-3-methylcyclopropyl ortetrafluorocyclobutyl), C₃-C₆-cycloalkyl-C₁-C₄-alkyl (eg.1-methylcyclopropyl, 2,2-dimethylcyclopropyl or 1-methylcyclohexyl),C₁-C₄-alkoxy-C₁-C₄-alkyl (eg. methoxymethyl, ethoxymethyl, n- orisopropoxymethyl, n-, iso-, sec- or tert-butoxymethyl,2-methoxyprop-2-yl, 2-ethoxyprop-2-yl, 2-n- or isopropoxyprop-2-yl or2-n-, iso-, sec- or tert-butoxyprop-2-yl), C₁-C₄-alkylthio-C₁-C₄-alkyl(eg. methylthiomethyl, ethylthiomethyl, n- or isopropylthiomethyl, n-,iso-, sec- ortert-butylthiomethyl,2-methylthioprop-2-yl,2-ethylthioprop-2-yl, 2-n- orisopropylthioprop-2-yl or 2-n-, iso-, sec- or tert-butylthioprop-2-yl),aryl(phenyl)thio-C₁-C₄-alkyl (eg. phenylthiomethyl or2-chlorophenylthiomethyl), C₂-C₆-alkenyl (eg. vinyl, 1-propenyl,2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl,3-methyl-2-butenyl or 2-methyl-2-penten-5-yl), C₂-C₅-haloalkenyl (eg.2,2-difluorovinyl, 2,2-dichlorovinyl, 3,3,3-trifluoropropenyl,3,3,3-trichloropropenyl or 3-chloro-2-propenyl), C₃-C₆-cycloalkenyl (eg.cyclopent-1-enyl, cyclopentadienyl or cyclohex-1-enyl),C₃-C₆-halocycloalkenyl (eg. pentafluorocyclopentadienyl orpentachlorocyclopentadienyl), C₂-C₄-alkynyl (eg. ethynyl, 1-propynyl or1-propargyl), C₁-C₄-alkoxy (eg. methoxy, ethoxy, n- or isopropoxy or n-,iso-, sec- or tert-butoxy), C₁-C₄-alkylthio (eg. methylthio, ethylthio,n- or isopropylthio or n-, iso-, sec- or tert-butylthio) or benzylthio,C₁-C₄-haloalkoxy (eg. trifluoromethoxy, pentafluoroethoxy or1,1,2,2-tetrafluoroethoxy),

N(R⁶)₂ (eg. amino, methylamino, dimethylamino, ethylamino, diethylamino,di-n-propylamino, diisopropylamino, di-n-butylamino or diisobutylamino),C₁-C₄-alkylcarbonyl (eg. acetyl, propionyl, butyryl, isobutyryl orpivaloyl),

unsubstituted or substituted phenylcarbonyl (eg. benzoyl or4-chlorobenzoyl),

unsubstituted or substituted benzylcarbonyl (eg.benzylcarbonyl),C₁-C₄-alkoxycarbonyl (eg. methoxycarbonyl, ethoxycarbonyl, n- orisopropoxycarbonyl or n-, iso-, sec- or tert-butoxycarbonyl),

unsubstituted or substituted phenoxycarbonyl (eq. phenoxycarbonyl or4-chlorophenoxycarbonyl),

unsubstituted or substituted benzyloxycarbonyl (eg. benzyloxycarbonyl),

—CO—N(R⁷)₂ (eg. aminocarbonyl, dimethylaminocarbonyl,diethylaminocarbonyl, diisopropylaminocarbonyl, phenylaminocarbonyl orN-methyl-N-phenylaminocarbonyl),

unsubstituted or substituted aryl (eg. phenyl, naphthyl or anthryl),

unsubstituted or substituted aryloxy (eg. phenoxy, naphthyloxy oranthryloxy),

unsubstituted or substituted arylthio (eg. phenylthio),

unsubstituted or substituted aryl-C₁-C₄-alkyl (eg. benzyl, 1-phenethyl,2-phenethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl,2-methyl-3-phenylpropyl, 2-methyl-2-phenylpropyl or 4-phenylbutyl),

unsubstituted or substituted aryl-C₁-C₄-alkenyl (eg. phenyl-1-ethenyl,2-phenyl-1-propenyl, 2,2-diphenylethenyl, 1-phenyl-1-propen-2-yl or1-phenyl-1-ethenyl),

unsubstituted or substituted aryloxy-C₁-C₄-alkyl (eg. phenoxymethyl),

unsubstituted or substituted arylthio-C₁-C₄-alkyl (eg.phenylthiomethyl),

unsubstituted or substituted hetaryl (eg. pyridyl, 2-pyridyl, 3-pyridyl,4-pyridyl, pyrimidinyl, 2,6-pyrimidinyl, 1,5-pyrimidinyl, thienyl,2-thienyl, 3-thienyl, furyl, 2-furyl, 3-furyl, 1-pyrrolyl, 1-imidazolyl,1,2,4-triazolyl, 1,3,4-triazolyl, 4-thiazolyl or 2-benzothiazolyl),

unsubstituted or substituted hetaryloxy (eg. 2-pyridyloxy or2-pyrimidinyloxy),

unsubstituted or substituted hetarylthio (eg. 2-pyridylthio,2-pyrimidinylthio or 2-benzothiazolylthio),

unsubstituted or substituted hetaryl-C₁-C₄-alkyl (eg. 2-pyridylmethyl or3-pyridylmethyl),

unsubstituted or substituted hetaryloxy-C₁-C₄-alkyl (eg.furfurylmethoxy, thienylmethoxy, 3-isoxazolylmethoxy, 2-oxazolylmethoxyor 2-pyridylmethoxy),

unsubstituted or substituted hetaryl-C₂-C₄-alkenyl (eg.2′-furyl-2-ethenyl, 2′-thienyl-2-ethenyl or 3′-pyridyl-2-ethenyl),

unsubstituted or substituted heterocyclyl (eg. oxiranyl, 1-aziridinyl,1-azetidinyl, 1-pyrrolidinyl, 2-tetrahydrofuryl, 2-tetrahydropyranyl,3-tetrahydropyranyl, 1-piperidinyl, 1-morpholinyl, 1-piperazinyl,1,3-dioxanyl or 3-tetrahydrothiopyranyl) or

unsubstituted or substituted heterocyclyloxy (eg. 2-dihydropyranyloxy or2-tetrahydropyranyloxy).

The radicals referred to above in connection with unsubstituted orsubstituted are, in addition to hydrogen, for example, fluorine,chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl,tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethyl,chloromethyl, dichloromethyl, trichloromethyl, trifluoromethoxy,1,1,2,2-tetrafluoroethoxy, methoximinomethyl, ethoximinomethyl,n-propoximinomethyl, n-butoximinomethyl,n-pentyloximinomethyl,n-hexyloximinomethyl, allyloximinomethyl,benzyloximinomethyl, isopropoximinomethyl, isobutoximinomethyl,tert-butoximinomethyl, methylimino-1-ethyl, ethoximino-1-ethyl,n-propoximino-1-ethyl, n-butoximino-1-ethyl, n-pentyloximino-1-ethyl,n-hexyloximino-1-ethyl, allyloximino-1-ethyl, benzyloximino-1-ethyl,phenyl, phenoxy, benzyloxy, imidazol-1-yl, piperazin-1-yl,4-morpholinyl, piperidin-1-yl, pyrid-2-yloxy, cyclopropyl, cyclohexyl,oxiranyl, 1,3-dioxan-2-yl, 1,3-dioxolan-2-yl andtetrahydropyran-2-yloxy.

The group

may also be the radical of a carbocyclic or heterocyclic oxime (eq.cyclopentanone oxime, cyclohexanone oxime, cycloheptanone oxime,2-adamantanone oxime, D-camphor oxime, 1-tetralone oxime, 1-indanoneoxime, 9-fluorenone oxime, 1-methyl-4-piperidone oxime, violuric acid orN,N-dimethylvioluric acid).

R³ and R⁴ together then form, for example, a cyclopentyl, cyclohexyl,cycloheptyl, adamantyl, camphenyl, tetralin, indane or fluorene ring.

One of the radicals R³ or R⁴ may furthermore be halogen (eg. fluorine,chlorine, bromine or iodine).

n may be 1, 2, 3 or 4 and R⁸ may be for example H, fluorine, chlorine,bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl,methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethyl, chloromethyl,dichloromethyl, trichloromethyl, trifluoromethoxy,1,1,2,2-tetrafluoromethoxy, phenyl, phenoxy, benzyloxy or pyrid-2-yl,where these radicals in turn may be substituted by fluorine, chlorine,bromine, iodine, cyano, methyl or methoxy.

Among the compounds in which R³ and R⁴ are hydrogen, the preferredcompounds are those in which either only R³ or only R⁴ is hydrogen, inparticular the compounds in which R³ is hydrogen.

Also preferred are compounds of the formula II in which X is CH₂, CHCH₃,CHC₂H₅, CHOCH₃, CHOC₂H₅, CHSCH₃ or CHSC₂H₅, Y is 0, R¹ is C₁-C₄-alkyl,R² is H or methyl, R³ and R⁴ are identical or different and each ishydrogen, cyano, straight-chain or branched C₁-C₁₀-alkyl,C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-alkylthio-C₁-C₄-alkyl, arylthio-C₁-C₄-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₂-C₄-haloalkenyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, substituted or unsubstitutedaryl, substituted or unsubstituted aryloxy, substituted or unsubstitutedarylthio, substituted or unsubstituted aryl-C₁-C₄-alkyl, substituted orunsubstituted aryl-C₂-C₄-alkenyl, substituted or unsubstitutedaryloxy-C₁-C₄-alkyl, substituted or unsubstituted hetaryl, substitutedor unsubstituted hetaryloxy, substituted or unsubstituted hetarylthio orsubstituted or unsubstituted heterocyclyl, or each is N(R⁶)₂, R⁶ beingidentical or different and denoting H, C₁-C₆-alkyl, C₃-C₆-cycloalkyl orsubstituted or unsubstituted phenyl, or each is —CO—N(R⁷)₂, R⁷ beingidentical or different and denoting H or C₁-C₄-alkyl, the term“substituted” denoting the radicals listed in claim 1, and R³ and R⁴ maytogether denote a carbocyclic or heterocyclic ring which may besubstituted by the radicals given under “substituted”, and R³ and R⁴ maybe halogen, and Z¹ and Z² are hydrogen, fluorine, chlorine, bromine,iodine, methyl, cyano or methoxy.

Owing to the C═C or C═N double bonds, the novel compounds of the generalformula I may be obtained in the preparation as E/Z isomer mixtures.These can be separated into the individual components in a conventionalmanner, for example by crystallization or chromatography.

Both the individual isomeric compounds and mixtures thereof formsubjects of the invention and can be used as pesticides.

The compounds of the general formula I as claimed in claim 1 areprepared, for example, as described in Scheme 1(Z¹ and Z² are each H).

The compounds of the general formula I in which X is CH₂, CH-alkyl orCH-alkoxy can be prepared, for example, from the ketoesters 4 by aWittig or Wittig-Horner reaction (cf. European Patents 348,766 and178,826 and DE 3 705 389). The similar compounds 5 are likewise obtainedfrom the ketoesters 2.

Alternatively, it is also possible to adopt a procedure in whichcompounds of the formula 7 or 9 are condensed with suitable reagents,for example with formaldehyde where X is CH₂ (cf. DE 3317356), a) withaldehydes (cf. D. M. Brown, J. Chem. Soc. 1948, 2147) or b) first withN,N-dimethylformamide dimethyl acetal, followed by reaction with aGrignard reagent (similarly to C. Jutz, Chem. Ber. 91 (1958), 1867)where X is CH-alkyl, or with a formate followed by alkylation (cf.European Patent 178,826) where X is CH—O-alkyl. Further preparationmethods for the compounds of the formula 5 and I where X is CH—O-alkylare described in European Patent 178,826.

Another possible method for preparing the compounds of the formula Iwhere X is CH-alkyl and YR₂ is COOAlk is to react ketene acetals withphenylchloro-carbenes (S. N. Slougui and G. Rousseau, Synth. Commun. 12(5) (1982), 401-407).

For compounds of the general formula I where X is CH—S-alkyl, thepreparation can be carried out by the methods described in EuropeanPatents 244,077 or 310,954.

The intermediates of the formulae 3, 6 and 8 can be prepared from thecompounds 2, 5 and 7 by halogenating the latter by a known method, forexample with chlorine, bromine or N-bromosuccinimide, in an inertsolvent (eg. CCl₄ or cyclohexane), with exposure to, for example, a Hgvapor lamp or in the presence of a free radical initiator, eg. dibenzoylperoxide, or by introducing the radicals L, eg. mesylate, tosylate,acetate or triflate, via suitable intermediates (where L is halogen orOH).

The oxime ethers of the formula I where X is N-Oalkyl can be preparedfrom 4 a) by reaction with an O-alkylhydroxylamine hydrochloride or b)with hydroxylamine hydrochloride and subsequent alkylation with analkylating agent (eg. an alkyl iodide, dialkyl sulfate, etc.) (cf. DE 3623 921).

Furthermore, a phenylacetic ester of the formula 9 can be converted witha base (eg. NaOMe, NaH, K tert-butylate, etc.) in a solvent (eg. diethylether, toluene, tert-butanol, etc.) by a method similar to that inEuropean Patent 254,426 into its anion and can be converted into theoxime with a suitable nitrosating agent (such as methyl nitrite, amylnitrate, tert-butyl nitrite, etc.). The resulting oximate is alkylatedwith an alkylating agent (eg. an alkyl iodide or dialkyl sulfate).

The same processes can also be applied to the compounds of the formulae2 and 7, and the resulting oxime ethers 5 can be converted in a knownmanner (European Patent 254,426) via the intermediates 6 (L is, forexample, halogen) into the desired compounds I.

In the preparation processes described above, Y—R¹ is usually alkoxy.

The compounds in which YR¹ is OH (11) can be prepared by methods knownfrom the literature (Organikum 16th edition, pages 415 and 622), fromthe compounds of the general formula I where YR¹ is COOAlkyl (10) (cf.Scheme 2):

Alternatively, the nitriles 12 can be converted in a known manner (cf.Organikum 16th edition, page 424 et seq. (1985) into the carboxylicacids 11.

The resulting carboxylic acids 11 can be converted in a conventionalmanner into the acyl chlorides 14 (cf. Organikum 16th edition, page 423et seq. (1985). The conversion of 14 into the amides 15 is effected bymethods similar to that described in Organikum 16th edition, page 412(1985).

The thioesters 13 are obtained from the acyl chlorides 14 (similarly toHouben-Weyl Vol. 8, page 464 et seq. (1952)).

Alternatively, the thioesters 13 can also be prepared from the acids 11(similarly to Houben-Weyl Vol. E5, page 855 et seq. (1985)).

The amides 15 in which R¹ and R⁵ are each H can also be prepared fromthe nitriles 12 by processes known from the literature (cf. Synthesis1980, 243).

The preparation of the compounds of the general formulae 2 and 7 withortho-methyl substitution at the aromatic (R²═H) is known.

(YR¹=OAlkyl; cf. European Patents 178,826 and 260,832).

The oximes required for the preparation of the compounds of the generalformula I are either known or can be prepared by one of the processesshown in Scheme 3.

Methods for the conversion of 16 or 18 into 17 are described inHouben-Weyl, Vol. 10/4 (1968).

Furthermore, aldoximes 19 can be chlorinated by known methods and can bereacted with, for example, a cyanide to give the derivatives 17 (R⁴═CN)(cf. M. R. Zimmermann J. f. prakt. Chemie 66 (1902), 359).

The specific derivatives in which R³ is CN and R⁴ is alkoxyalkyl areprepared according to European Patent 74,047, those in which R³ is CNand R⁴ is alkylthioalkyl according to European Patent 150,822 and thosein which R³ is CN and R⁴ is alkyl according to DE 2 304 848.

The method employing Me₃SiO—NH—SiMe₃ (R. U. Hoffmann and G. A. Buntain,Synthesis 1987, 831) is used for sterically hindered ketones.

The novel compounds of the general formula I as claimed in claim 1 areprepared, for example, by a method in which an oxime of the formula 17is reacted with a substituted benzyl compound 6 in which L is a leavinggroup (eg. chloride, bromide, p-toluenesulfonate, methanesulfonate,triflate or acetate). R¹-R⁴, X and Y have the abovementioned meanings.

The reactions described can be carried out, for example, in an inertsolvent (eg. acetone, acetonitrile, dimethyl sulfoxide,dimethylformamide, N-methylpyrrolidone or pyridine) with the use of abase (eg. sodium carbonate, potassium carbonate, sodium hydroxide,potassium hydroxide, sodium hydride or sodium methylate).

The reactions can also be carried out in a two-phase system (eg.dichloromethane or water) with the aid of a suitable phase transfercatalyst (eg. cetyltrimethylammonium chloride or benzyltrimethylammoniumchloride).

Another method for the preparation of compounds I (YR¹=OAlkyl,X═CH-OAlkyl or N-OAlkyl and L═Cl, Br, tosylate or mesylate) isillustrated by Scheme 5:

This synthesis sequence is carried out, as far as compound 22, similarlyto the methods described in European Patent 244,786.

For example, N-hydroxyphthalimide can be converted with a halide orsulfonic ester 6 in the presence of an acid acceptor (eg. triethylamine,potassium carbonate, etc.), in a suitable solvent (eg.N-methylpyrrolidone, dimethylformamide, etc.), into the imidoether 21.

Cleavage to give the O-substituted hydroxylamine 22 can be effected witha mineral acid (eg. HCl; cf. Houben-Weyl Vol. 10/1, page 1181 et seq.)or with a base (for example with hydrazine or ethanolamine).

The conversion of amine 22 to I is carried out in a conventional manner(cf. D. Otzanak, J.C.S. Chem. Commun. 1986, 903).

The Examples and methods which follow are intended to illustrate thepreparation of the novel active ingredients and of the novelintermediates.

Method 1

3,4-Dichloroacetophenone oxime

12.0 g (0.17 mol) of hydroxylammonium hydrochloride and 18.9 g (0.1 mol)of 3,4-dichloroacetophenone are added to a mixture of 20 ml of H₂O, 100ml of methanol and 8 g (0.1 mol) of pyridine. Refluxing is carried outfor 1 hour, after which the mixture is acidified with 2 N HCl andextracted with 3×100 ml of tert-butyl methyl ether. The organic phase iswashed with water, dried with Na₂SO₄ and evaporated down. 19.6 g (96% oftheory) of crystals of melting point 92° C., which according to ¹H-NMRconsist of 90% of trans-oxime, are obtained.

Method 2

2-Oximino-2-tetrahydropyran-2′-ylacetonitrile

265.4 g (2.05 mol) of tetrahydrofuran-2-carbaldehyde oxime in 2 l ofdiethyl ether are initially taken at from −55 to −60° C. 153.5 g (2.15mol) of chlorine are then passed in and the temperature is increased to−20° C.; stirring is carried out for 1 hour, the mixture is thenevaporated down in a rotary evaporator at 10° C., the residue is takenup in 1.5 l of diethyl ether and the solution is stirred overnight inthe absence of light, while cooling with ice. The solution is thenfiltered and the filtrate is added dropwise, while cooling with ice, to147.3 g (2.27 mol) of potassium cyanide in 1 l of methanol at 10-15° C.(exothermic). Stirring is carried out for 5 hours at room temperature(20° C.), after which the precipitate is filtered off under suction andwashed twice with diethyl ether. The organic phases are partitionedbetween tert-butyl methyl ether and water and the residue of the etherphases is crystallized from dichloromethane/n-hexane at 0° C.

After filtration under suction and drying, 208 g (66% of theory) of aspectroscopically pure substance of melting point 105-106° C. remain.

Method 3

3-Methoxy-3-methyl-2-oximinobutyronitrile

53.6 g (0.46 mol) of 2-methoxy-2-methylpropionaldehyde oxime in ether(about 1 M) are initially taken at from −5 to −10° C. 35.8 g (0.5 mol)of chlorine gas are passed in, after which stirring is carried out for 1hour at this temperature and the mixture is then evaporated down at 10°C. and the residue is taken up in diethyl ether. 24.7 g (0.5 mol) ofsodium cyanide in 375 ml of 20:1 methanol/H₂O are initially taken at 10°C. and the above ethereal solution is rapidly added dropwise. After 4hours at room temperature, the mixture is filtered under suction and theresidue is washed with twice 100 ml of methanol. The combined solutionsare evaporated down and the residue is partitioned between methyltert-butyl ether and water. Drying the organic phase over Na₂SO₄,evaporating down and crystallizing from dichloromethane-/n-hexane give41.1 g (63% of theory) of a white powder of melting point 102-104° C.

Method 4

Methyl 3-methoxy-2-[2′-(phthalimido-oxy)-methyl]-phenylacrylate

10 g (35 mmol) of methyl 3-methoxy-2-(2′-bromomethyl)-phenylacrylate,5.7 g (35 mmol) of hydroxyphthalimide, 3.9 g (38.6 mmol) oftriethylamine and 50 ml of N-methylpyrrolidone are combined and themixture is stirred for 2 hours at 60° C. It is then poured onto icewater, and the residue is filtered off under suction, washed with waterand isopropanol and dried under reduced pressure. 9.0 g (70% of theory)of a crystalline product of melting point 156-158° C. remain.

¹H-NMR (CDCl₃): δ=3.60 (s, 3H); 3.75 (s, 3H); 5.12 (s, 2H); 7.13 (dbr,1H); 7.35 (m, 2H); 7.62 (s, 1H); 7.7-7.9 (m, 5H)

Method 5

Methyl 3-methoxy-2-(2′-aminooxymethyl)-phenylacrylate

10.0 g (27 mmol) of the product from Method 4 are dissolved in 150 ml ofmethanol and the solution is stirred with 1.4 g (27 mmol) of hydrazinehydrate for 2 hours at room temperature. The precipitate is filtered offunder suction, the mother liquor is evaporated down, the residue isstirred with diethyl ether, the precipitate is filtered off undersuction again and the mother liquor is evaporated down. 6.0 g (92% oftheory) of a yellow oil result (purity according to ¹H-NMR about 90%).

¹H-NMR (CDCl₃): δ=3.71 (s, 3H); 3.80 (s, 3H); 4.60 (s, 2H); (5.35 (sbr,2H); 7.0-7.50 (m, 4H); 7.58 (s, 1H).

Method 6

Methyl 2-methoximino-2-(2′-phthalimidooxymethyl)-phenylacetate

2.0 g (7 mmol) of methyl 2-methoximino-2-(2′-bromomethyl)-phenylacetate,1.1 g (7 mmol) of hydroxyphthalimide and 0.8 g (7.7. mmol) oftriethylamine are dissolved in 10 ml of N-methylpyrrolidone and thesolution is stirred for 2 hours at 70° C. For working up, ice water isadded, and the crystals are filtered off under suction, washed withwater and methyl tert-butyl ether and dried.

1.5 g (58% of theory) of crystals of melting point 152-155° C. remain.

¹H-NMR (CDCl₃): δ=3.83 (s, 3H); 3.98 (s, 3H); 5.07 (s, 2H); 7.15 (dbr,1H); 7.45 (mc, 2H); 7.60-7.85 (m, 5H)

Method 7

Methyl 2-methoximino-2-(2′-aminooxymethyl)-phenylacetate

15.0 g (41 mmol) of the product from Method 6 are stirred with 2.1 g (42mmol) of hydrazine hydrate in 150 ml of methanol for 2 hours at roomtemperature. The residue is again filtered off under suction, the motherliquor is evaporated down and triturated with diethyl ether, the residueis filtered off under suction and the mother liquor is evaporated down.7.8 g (80% of theory) of an acid-sensitive oil remain.

¹H-NMR (CDCl₃): δ=3.90 (s, 3H); 4.03 (s, 3H); 4.59 (s, 2H); 5.35 (sbr,2H); 7.15 (dbr, 1H); 7.40 (sbr, 3H)

EXAMPLE 1 Methyl3-methoxy-2-[2′-[1″-(3′″,5′″-dichlorophenyl)-1″-methyl]-iminooxymethyl]-phenylacrylate(No. 582, Table I)

0.6 g (25 mmol) of sodium hydride powder in 100 ml of acetonitrile isinitially taken, 5.1 g (25 mmol) of 3,5-dichloroacetophenone oxime areadded and the mixture is refluxed for 1 hour. Thereafter, 9.3 g (33mmol) of methyl 2-(2′-bromomethyl)-phenyl-3-methoxyacrylate in 50 ml ofacetonitrile are added dropwise and refluxing is continued for a further4 hours. The mixture is evaporated down under reduced pressure and thenpartitioned between methyl tert-butyl ether and saturated ammoniumchloride solution, the organic phase is washed with water and theresidue obtained by evaporation is crystallized from methyl butylether/n-hexane. 4.6 g (45% of theory) of a substance of melting point87-88° C. are obtained.

¹H-NMR (CDCl₃): δ=2.19 (s, 3H); 3.70 (s, 3H); 3.81 (s, 3H); 5.15 (s,2H); 7.08 (m, 1H); 7.17 (m, 3H); 7.50 (m, 3H); 7.58 (s, 1H)

EXAMPLE 2 Methyl3-methoxy-2-[2′-(1″-cyano-(-1″-methoxy-1″-methylethyl)-iminooxymethyl]-phenylacrylate(No. 36, Table I)

3.3 g (23 mmol) of 3-methoxy-3-methyl-2-oximinobutyronitrile, 6.6 g (23mmol) of methyl 2-(2′-bromomethylphenyl)-3-methoxyacrylate and 3.2 g (23mmol) of potassium carbonate in 60 ml of N,N-dimethylformamide arestirred for 15 hours at room temperature. The mixture is then evaporateddown, the residue is taken up in ethyl acetate, the solution is washedwith 3×50 ml of water and the organic phase is dried over sodiumsulfate, evaporated down and chromatographed over silica gel using 40:1toluene/ethyl acetate.

Yield: 7.0 g (88% of theory) of an oil.

IR (film): 1,285, 1,258, 1,189, 1,180, 1,131, 1,111, 1,069, 1,008 cm⁻¹.

EXAMPLE 3 Methyl2-methoximino-2-[2′-(1″-(3′″,5′″-dichlorophenyl)-1″-methyl)-iminooxymethyl]-phenylacetate(No. 582, Table II)

0.6 g (25 mmol) of NaH in 50 ml of acetonitrile is initially taken, and5.1 g (25 mmol) of 3,5-dichloroacetophenone oxime are added at roomtemperature. Refluxing is carried out for 1 hour, after which 9.4 g (33mmol) of methyl 2-methoximino-2-(2′-bromomethyl)-phenylacetate in 50 mlof acetonitrile are added dropwise and refluxing is continued for afurther 4 hours. After evaporating down, partitioning the residuebetween water/methyl tert-butyl ether, washing the organic phase withwater, drying the organic phase with sodium sulfate and evaporatingdown, the residue is subjected to column chromatography over silica gelusing methyl tert-butyl ether/hexane. 5.4 g (53% of theory) of crystalsof melting point 95-97° C. result.

¹H-NMR (CDCl₃): δ=2.17 (s, 3H); 3.82 (s, 3H); 4.02 (s, 3H); 5.15 (s,2H); 7.20 (dbr, 1H); 7.25-7.55 (m, 6H)

EXAMPLE 4 Methyl3-methoxy-2-[2′-(1″-(4′″-bromophenyl)-1″-methyl)-iminooxymethyl]-phenylacrylate(No. 593, Table I)

2.37 g (10 mmol) of methyl3-methoxy-2-(2′-aminooxymethyl)-phenylacrylate, 1.99 g (10 mmol) of4-bromoacetophenone, 2 ml of water, 0.8 g of pyridine and 10 ml ofmethanol are combined and the mixture is stirred for 24 hours at roomtemperature. The mixture is evaporated down, the residue is partitionedbetween water/methyl tert-butyl ether and the organic phase is washedwith 2 N HCl and washed neutral with NaHCO₃ and evaporated down, and theresidue is chromatographed over SiO₂ using methyl tert-butylether/hexane. 2.1 g (51% of theory) of crystals of melting point105-107° C. result.

¹H-NMR (CDCl₃): δ=2.22 (s, 3H); 3.70 (s, 3H); 3.80 (s, 3H); 5.15 (s,2H); 7.16 (dbr, 1H); 7.33 (m, 2H); 7.45 (m, 5H); 7.58 (s, 1H)

EXAMPLE 5 Methyl2-methoximino-2-[2′-(1″-(4′″-nitrophenyl)-1″-methyl)-iminooxymethyl]-phenylacetate(No. 614, Table II)

2.38 g (10 mmol) of methyl2-methoximino-2-(2′-aminooxymethyl)-phenylacetate, 1.65 g (10 mmol) of4-nitroacetophenone, 2 ml of water, 0.8 g of pyridine and 10 ml ofmethanol are reacted as in Example 4. 2.1 g (55% of theory) of crystalsof melting point 87-89° C. are obtained.

¹H-NMR (CDCl₃): δ=2.22 (s, 3H); 3.81 (s, 3H); 4.02 (s, 3H); 5.18 (s,2H); 7.20 (dd, 1H); 7.4 (m, 3H); 7.75 (dd, 2H); 8.18 (dd, 2H).

EXAMPLE 6 Methyl3-methoxy-2-[2′-(1″-(4′″-chlorophenyl)-iminooxymethyl]-phenylacrylate(No. 95 Table 5)

a) 5.5 g (15 mmol) of methyl3-methoxy-2-[2′-(phthalimidooxy)-methyl]-phenylacrylate (from Method 4)in 100 ml of methanol are initially taken, and 0.75 g (15 mmol) ofhydrazine hydrate is added at room temperature. After 15 minutes at thistemperature, the mixture is evaporated down, the residue is trituratedwith methyl tert-butyl ether and the cleavage product is filtered offunder suction. The mother liquor is evaporated down, the residue istaken up with 50 ml of methanol and 2.1 g (15 mmol) of4-chlorobenzaldehyde in 50 ml of methanol plus 1 drop of pyridine areadded dropwise.

Stirring was carried out overnight at 23° C., after which the productwas filtered off under suction, washed with methanol and dried.

2.9 g (54% of theory) of crystals of melting point 87-89° C. wereobtained.

¹H-NMR (CDCl₃): δ=3.66 (s, 3H); 3.80 (s, 3H); 5.13 (s, 2H); 7.17 (m,1H); 7.35 (m, 4H); 7.50 (me, 3H); 7.60 (s, 1H); 8.06 (s, 1H).

b) 50 ml of methanol are slowly added to 1.3 g (55 mmol) of NaH powderunder a nitrogen atmosphere (evolution of hydrogen). 7.8 g (50 mmol) of4-chlorobenzaldehyde oxime in 50 ml of methanol are then added at roomtemperature. Stirring is carried out for half an hour, after which 14.3g (50 mmol) of methyl 3-methoxy-2-(2′-bromomethyl)-phenylacrylate in 50ml of methanol are added dropwise and stirring is carried out at roomtemperature for a further 48 hours. The white residue is filtered offunder suction, washed with methanol and dried. 1.9 g (11% of theory) ofa product of melting point 82-84° C. are obtained.

EXAMPLE 7 Methyl 2-methoximino-2-(2′-phthalimidooxymethyl)-phenylacetate(No. 1, Table 8)

2.0 g (7 mmol) of methyl2-methoxyimino-2-(2′-bromomethyl)-phenylacetate, 1.1 g (7 mmol) ofhydroxyphthalimide and 0.8 g (7.7 mmol) of triethylamine are dissolvedin 10 ml of N-methylpyrrolidone and the mixture is stirred for 2 hoursat 70° C. Ice water is added and the crystals are filtered off undersuction, washed with water and methyl tert-butyl ether and dried. Thereremain 1.5 g (58% of theory) of crystals of melting point 152-155° C.

1H-NMR (CDCl₃): δ=3.83 (s, 3H); 3.98 (s, 3H); 5.07 (s, 2H); 7.15 (dbr,1H); 7.45 (mc, 2H); 7.60-7.85 (m, 5H).

The compounds listed in Tables I-IX can be prepared in a similar manner.

TABLE I

No. R₃ R₄ Data  1 Cl Phenyl  2 Cl Cyano  3 Cl Ethoxycarbonyl  4 ClCyclopropyl  5 CF₃ CF₃  6 CF₃ Phenyl  7 CCl₃ CCl₃  8 CCl₃ Phenyl  9CH₂Cl Phenyl  10 CF₂CF₃ Phenyl  11 CF₂Cl Phenyl  12 CHCl₂ Phenyl  13Cyclopropyl Cyclopropyl  14 Cyclopropyl Phenyl oil; IR (film): 1190,1129, 1056, 1032, 768  15 Cyclopropyl 4-Fluorophenyl oil; IR (film):1508, 1225, 1129, 998, 839  16 Cyclopropyl 4-Chlorophenyl oil; IR(film): 1490, 1129, 1091, 1014, 1800  17 Cyclopropyl 4-Methoxyphenyloil; IR (film): 1251, 1177, 1129, 1033  18 Cyclopropyl 4-Ethoxyphenyl 19 Cyclopropyl 4-Phenoxyphenyl  20 Cyclopropyl Pentachlorophenyl  21Cyclopropyl Pentachlorophenyl  22 Cyclopropyl Phenyl  23 CyclohexylPhenyl  24 Phenyl 2,2-Dichloro-1-methylcyclopropyl  25 Phenyl2,2-Difluorocyclopropyl  26 Phenyl 2,2-Dichlorocyclopropyl  27 Phenyl2,2-Dibromocyclopropyl  28 Phenyl 2,2,3,3-Tetrafluorocyclobutyl  29Phenyl 2,2-Dimethylcyclopropyl  30 Phenyl 1-Methylclohexyl  31 CNMethoxymethyl  32 CN Ethoxymethyl  33 CN n-Propoxymethyl  34 CNiso-Propoxymethyl  35 CN tert.-Butoxymethyl  36 CN 2-Methoxyprop-2-yloil; IR (film): 1436, 1191, 1131, 1057, 1003  37 CN 2-Ethoxyprop-2-yloil; IR (film): 1191, 1177, 1131, 1095, 1010  38 CN 2-n-Propoxyprop-2-yloil; IR (film): 1191, 1175, 1131, 1060, 1005  39 CN2-iso-Propoxyprop-2-yl oil; IR (film): 1370, 1191, 1172, 1131, 998  40CN 2-tert.-Butoxyprop-2-yl  41 CN Methylthiomethyl  42 CNtert-Butylthiomethyl  43 CN 2-Methylthioprop-2-yl oil; IR (film): 1436,1191, 1131, 1114, 1016, 998  44 CN 2-iso-Propylthioprop-2-yl  45 CN2-tert.-Butylthioprop-2-yl oil; IR (film): 1366, 1191, 1132, 1113, 1012,1000  46 CN Methyl  47 CN Ethyl  48 CN n-Propyl  49 CN iso-Propyl oil;IR (film): 1285, 1258, 1189, 1131, 1111, 1069, 1008  50 CN n-Butyl  51CN iso-Butyl  52 CN sec.-Butyl  53 CN tert.-Butyl  54 CN n-Hexyl  55 CNn-Decyl  56 CN Cyclopropyl oil; IR (film): 1207, 1190, 1130, 1057, 1003 57 CN Cyclohexyl  58 CN Phenylthiomethyl  59 CN 2-Phenylthiomethyl  60CN 2-(2′-Chlorophenylthio)prop-2-yl  61 CN Ethynyl  62 CN 1-Propynyl  63CN Methoxy  64 CN Ethoxy  65 CN n-Propoxy  66 CN iso-Propoxy  67 CNn-Butoxy  68 CN iso-Butoxy  69 CN sec.-Butoxy  70 CN tert.-Butoxy  71 CNMethylthio  72 CN Ethylthio  73 CN n-Propylthio  74 CN iso-Propylthio 75 CN n-Butylthio  76 CN iso-Butylthio  77 CN sec.-Butylthio  78 CNtert.-Butylthio  79 CN Benzylthio  80 CN Trifluoromethoxy  81 CN Cyano 82 CN Amino  83 CN Methylamino  84 CN Dimethylamino  85 CN Ethylamino 86 CN Diethylamino  87 CN Di-n-Propylamino  88 CN Di-iso-Propylamino 89 CN Di-n-Butylamino  90 CN Di-iso-Butylamino  91 CN Acetyl  92 CNPropion-1-yl  93 CN Butyr-1-yl  94 CN Iso-Butyr-1-yl  95 CN Pivaloyl  96CN Benzoyl  97 CN 4-Chlorobenzoyl  98 CN Benzylcarbonyl  99 CNMethoxycarbonyl 100 CN Ethoxycarbonyl 101 CN n-Propoxycarbonyl 102 CNiso-Propoxycarbonyl 103 CN n-Butoxycarbonyl 104 CN iso-Butoxycarbonyl105 CN sec.-Butoxycarbonyl 106 CN tert.-Butoxycarbonyl 107 CNn-Hexoxycarbonyl 108 CN Phenoxycarbonyl 109 CN 4-Chlorophenoxycarbonyl110 CN Benzyloxycarbonyl 111 CN Aminocarbonyl 112 CNDimethylaminocarbonyl 113 CN Diethylaminocarbonyl 114 CNDi-iso-Propylaminocarbonyl 115 CN Phenylaminocarbonyl 116 CNN-Methyl-N-Phenylaminocarbonyl 117 CN Phenyl oil; IR (film): 1245, 1127,1024, 1015, 767, 750 118 CN 2-Fluorophenyl 119 CN 3-Fluorophenyl 120 CN4-Fluorophenyl 121 CN Pentafluorophenyl 122 CN 2-Chlorophenyl 123 CN3-Chlorophenyl 124 CN 4-Chlorophenyl 125 CN Pentachlorophenyl 126 .CN2,3-Dichlorophenyl 127 CN 2,4-Dichlorophenyl 128 CN 2,5-Dichlorophenyl129 CN 2,6-Dichlorophenyl 130 CN 3,4-Dichlorophenyl 131 CN3,5-Dichlorophenyl 132 CN 2,3,4-Trichlorophenyl 133 CN2,3,5-Trichlorophenyl 134 CN 2,3,6-Trichlorophenyl 135 CN2,4,5-Trichlorophenyl 136 CN 2,4,6-Trichlorophenyl 137 CN3,4,5-Trichlorophenyl 138 CN 2,3,4,6-Tetrachlorophenyl 139 CN2,3,5-6-Tetrachlorophenyl 140 CN 2-Bromophenyl 141 CN 3-Bromophenyl 142CN 4-Bromophenyl 143 CN 2,4-Dibromophenyl 144 CN 3-Bromo-4-fluorophenyl145 CN 3-Bromo-4-methoxyphenyl 146 CN 2-Iodophenyl 147 CN 3-Iodophenyl148 CN 4-Iodophenyl 149 CN 2-Chloro-4-fluorophenyl 150 CN2-Chloro-5-fluorophenyl 151 CN 2-Chloro-6-fluorophenyl 152 CN2-Chloro-4-bromophenyl 153 CN 2-Bromo-4-chlorophenyl 154 CN2-Bromo-4-fluorophenyl 155 CN 3-Bromo-4-chlorophenyl 156 CN3-Chloro-4-fluorophenyl 157 CN 3-Fluoro-4-chlorophenyl 158 CN2-Cyanophenyl 159 CN 3-Cyanophenyl 160 CN 4-Cyanophenyl 161 CN2-Nitrophenyl 162 CN 3-Nitrophenyl 163 CN 4-Nitrophenyl 164 CN2-Methylphenyl 165 CN 3-Methylphenyl 166 CN 2-Methylphenyl 167 CN214-Dimethylphenyl 168 CN 2,6-Dimethylphenyl 169 CN 3,4-Dimethylphenyl170 CN 3,5-Dimethylphenyl 171 CN 2,3,4-Trimethylphenyl 172 CN2,3,5-Trimethylphenyl 173 CN 2,3,6-Trimethylphenyl 174 CN2,4,5-Trimethylphenyl 175 CN 2,4,6-Trimethylphenyl 176 CN3,4,5-Trimethylphenyl 177 CN Pentamethylphenyl 178 CN 2-Ethylphenyl 179CN 3-Ethylphenyl 180 CN 4-Ethylphenyl 181 CN 3,5-Diethylphenyl 182 CN2-n-Propylphenyl 183 CN 3-n-Propylphenyl 184 CN 4-n-Propylphenyl 185 CN2-iso-Propylphenyl 186 CN 3-iso-Propylphenyl 187 CN 4-iso-Propylphenyl188 CN 2,4-Di-iso-Propylphenyl 189 CN 3,5-Di-iso-Propylphenyl 190 CN4-n-Butylphenyl 190 CN 4-sec.-Butylphenyl 192 CN 4-iso-Butylphenyl 193CN 4-tert.-Butylphenyl 194 CN 3-tert.-Butylphenyl 195 CN2-tert.-Butylphenyl 196 CN 2,4-Di-tert.-Butylphenyl 197 CN3,5-Di-tert.-Butylphenyl 198 CN 4-n-Hexylphenyl 199 CN 4-n-Dodecylphenyl200 CN 2-Methyl-4-tert.-Butylphenyl 201 CN 2-Methyl-6-tert.-Butylphenyl202 CN 2-Methyl-4-iso-Propylphenyl 203 CN 2-Methyl-4-Cyclohexylphenyl204 CN 2-Methyl-4-Phenylphenyl 205 CN 2-Methyl-4-Benzylphenyl 206 CN2-Methyl-4-Phenoxyphenyl 207 CN 2-Methyl-4-Benzyloxyphenyl 208 CN2-Methyl-3-Chlorophenyl 209 CN 2-Methyl-4-Chlorophenyl 210 CN2-Methyl-5-Chlorophenyl 211 CN 2-Methyl-6-Chlorophenyl 212 CN2-Methyl-4-Fluorophenyl 213 CN 2-Methyl-3-Bromophenyl 214 CN2-Methyl-4-Bromophenyl 215 CN 2-Methyl-3-Methoxyphenyl 216 CN2-Methyl-4-Methoxyphenyl 217 CN 2-Methyl-5-methoxyphenyl 218 CN2-Methyl-6-methoxyphenyl 219 CN 2-Methyl-4-iso-Propoxyphenyl 220 CN2-Methyl-2,5-dimethoxyphenyl 221 CN 2-Methoxyphenyl 222 CN3-Methoxyphenyl 223 CN 4-Methoxyphenyl 224 CN 2,3-Dimethoxyphenyl 225 CN2,4-Dimethoxyphenyl 226 CN 2,5-Dimethoxyphenyl 227 CN2,6-Dimethoxyphenyl 228 CN 3,4-Dimethoxyphenyl 229 CN3,5-Dimethoxyphenyl 230 CN 3,6-Dimethoxyphenyl 231 CN2,3,4-Trimethoxyphenyl 232 CN 2,3,5-Trimethoxyphenyl 233 CN2,3,6-Trimethoxyphenyl 234 CN 2,4,5-Trimethoxyphenyl 235 CN2,4,6-Trimethoxyphenyl 236 CN 3,4,5-Trimethoxyphenyl 237 CN2-Ethoxyphenyl 238 CN 3-Ethoxyphenyl 239 CN 4-Ethoxyphenyl 240 CN2-iso-Propoxyphenyl 241 CN 3-iso-Propoxyphenyl 242 CN4-iso-Propoxyphenyl 243 CN 3-tert.-Butoxyphenyl 244 CN4-tert.-Butoxyphenyl 245 CN 2-Trifluoromethoxyphenyl 246 CN3-Trifluoromethoxyphenyl 247 CN 4-Trifluoromethoxyphenyl 248 CN 3-(1′,1′, 2′,2′-Tetrafluoro)ethoxyphenyl 249 CN 4-(1′, 1′,2′,2′-Tetrafluoro)ethoxyphenyl 250 CN 2-Chloromethylphenyl 251 CN3-Chloromethylphenyl 252 CN 4-Chloromethylphenyl 253 CN2-Trifluoromethylphenyl 254 CN 3-Trifluoromethylphenyl 255 CN4-Trifluoromethylphenyl 256 CN 2-(Methoxyiminomethyl)phenyl 257 CN3-(Methoxyiminomethyl)phenyl 258 CN 4-(Methoxyiminomethyl)phenyl 259 CN2-(Ethoxyiminomethyl)phenyl 260 CN 3-(Ethoxyiminomethyl)phenyl 261 CN4-(Ethoxyiminomethyl)phenyl 262 CN 2-(n-Propoxyiminomethyl)phenyl 263 CN3-(n-Propoxyiminomethyl)phenyl 264 CN 4-(n-Propoxyiminoniethyl)phenyl265 CN 2-(iso-Propoxyiminomethyl)phenyl 266 CN3-(iso-Propoxyiminomethyl)phenyl 267 CN 4-(iso-Propoxyiminomethyl)phenyl268 CN 2-(n-Butoxyiminomethyl)phenyl 269 CN3-(n-Butoxyiminomethyl)phenyl 270 CN 4-(n-Butoxyiminomethyl)phenyl 271CN 2-(iso-Butoxyiminomethyl)phenyl 272 CN3-(iso-Butoxyiminomethyl)phenyl 273 CN 4-(iso-Butoxyiminomethyl)phenyl274 CN 2-(tert.-Butoxyiminomethyl)phenyl 275 CN3-(tert.-Butoxyiminomethyl)phenyl 276 CN4-(tert.-Butoxyiminomethyl)phenyl 277 CN 2-(n-Pentoxyiminomethyl)phenyl278 CN 3-(n-Pentoxyiminomethyl)phenyl 279 CN4-(n-Pentoxyiminomethyl)phenyl 280 CN 2-(n-Hextoxyiminomethyl)phenyl 281CN 3-(n-Hextoxyiminomethyl)phenyl 282 CN 4-(n-Hextoxyiminomethyl)phenyl283 CN 2-(Allyloxyiminomethyl)phenyl 284 CN3-(Allyloxyiminomethyl)phenyl 285 CN 4-(Allyloxyiminomethyl)phenyl 286CN 2-(Benzyloxyiminomethyl)phenyl 287 CN 3-(Benzyloxyiminomethyl)phenyl288 CN 4-(Benzyloxyiminomethyl)phenyl 289 CN2-(Methoxyimino(1′-ethyl)phenyl 290 CN 3-(Methoxyimino(1′-ethyl)phenyl291 CN 4-(Methoxyimino(1′-ethyl)phenyl 292 CN2-(Ethoxyimino(1′-ethyl)phenyl 293 CN 3-(Ethoxyimino(1′-ethyl)phenyl 294CN 4-(Ethoxyimino(1′-ethyl)phenyl 295 CN2-(n-Propoxyimino(1′-ethyl)phenyl 296 CN3-(n-Propoxyimino(1′-ethyl)phenyl 297 CN4-(n-Propoxyimino(1′-ethyl)phenyl 298 CN2-(n-Butoxyimino(1′-ethyl)phenyl 299 CN 3-(n-Butoxyimino(1′-ethyl)phenyl300 CN 4-(n-Butoxyimino(1′-ethyl)phenyl 301 CN2-(n-Pentoxyimino(1′-ethyl)phenyl 302 CN3-(n-Pentoxyimino(1′-ethyl)phenyl 303 CN4-(n-Pentoxyimino(1′-ethyl)phenyl 304 CN2-(n-Hexoxyimino(1′-ethyl)phenyl 305 CN 3-(n-Hexoxyimino(1′-ethyl)phenyl306 CN 4-(n-Hexoxyimino(1′-ethyl)phenyl 307 CN2-(n-Allyloxyimino(1′-ethyl)phenyl 308 CN3-(n-Allyloxyimino(1′-ethyl)phenyl 309 CN4-(n-Allyloxyimino(1′-ethyl)phenyl 310 CN2-(n-Benzyloxyimino(1′-ethyl)phenyl 311 CN3-(n-Benzyloxyimino(1′-ethyl)phenyl 312 CN4-(n-Benzyloxyimino(1′-ethyl)phenyl 313 CN 2-Phenylphenyl 314 CN3-Phenylphenyl 315 CN 4-Phenylphenyl 316 CN 2-Phenoxyphenyl 317 CN3-Phenoxyphenyl 318 CN 4-Phenoxyphenyl 319 CN 2-Benzoxyphenyl 320 CN3-Benzoxyphenyl 321 CN 4-Benzoxyphenyl 322 CN 4-(Imidazol-1′-yl)phenyl323 CN 4-(Piperazin-1′-yl)phenyl 324 CN 4-(Morpholin-1′-yl)phenyl 325 CN4-(Piperadin-1′-yl)phenyl 326 CN 4-(Piperidyl-2′-oxy)phenyl 327 CN2-Cyclopropylphenyl 328 CN 3-Cyclopropylphenyl 329 CN4-Cyclopropylphenyl 330 CN 3-Cyclohexylphenyl 331 CN 4-Cyclohexylphenyl332 CN 4-Oxiranylphenyl 333 CN 4-(1-40 ,3-40 -Dioxan-2′yl)phenyl 334 CN4-(Tetrahydropyran-2-yloxy)phenyl 335 CN 1-Naphthyl 336 CN 2-Naphthyl337 CN 9-Anthryl 338 CN 1-Naphtoxy 339 CN 2-Naphtoxy 340 CN 9-Anthroxy341 CN Phenoxy 342 CN 2-Chlorophenoxy 343 CN 3-Chlorophenoxy 344 CN4-Chlorophenoxy 345 CN 4-Methylphenoxy 346 CN 4-tert.-Butylphenoxy 347CN 4-Methoxyphenoxy 348 CN 4-Ethoxyphenoxy 349 CN 4-tert.-Butoxyphenoxy350 CN Phenylthio 351 CN 2-Chlorophenylthio 352 CN 4-Chlorophenylthio353 CN Benzyl 354 CN 2-Methylbenzyl 355 CN 3-Methylbenzyl 356 CN4-Methylbenzyl 357 CN 4-tert.-Butylbenzyl 358 CN 2-Chlorobenzyl 359 CN3-Chlorobenzyl 360 CN 4-Chlorobenzyl 361 CN 2,4-Dichlorobenzyl 362 CN2,6-Dichlorobenzyl 363 CN 2,4,6-Trichlorobenzyl 364 CN2-Trifluoromethylbenzyl 365 CN 3-Trifluoromethylbenzyl 366 CN4-Trifluoromethylbenzyl 367 CN 2-Methoxybenzy 368 CN 4-Methoxybenzy 369CN 4-tert.-Butoxybenzyl 370 CN 4-Phenoxybenzyl 371 CN 1-Phenethyl 372 CN1-Phenylpropyl 373 CN 1-Phenethyl 374 CN 2-Phenethyl 375 CN 3-Phenethyl376 CN 2-Methyl-2-phenylpropyl 377 CN 2-Methyl-3-phenylpropyl 378 CN4-Phenylbutyl 379 CN 2-Phenyl-1-ethenyl 380 CN 1-Phenyl-1-ethenyl 381 CN1-Phenyl-1-propenyl 382 CN 1-Phenyl-1-propen-2-yl 383 CN2,2-Diphenylethenyl 384 CN Phenoxymethyl 385 CN 2-Pyridyl 386 CN3-Pyridyl 387 CN 4-Pyridyl 388 CN 2,6-Pyrimidinyl 389 CN 1,5-Pyrimidinyl390 CN 2-Thienyl 391 CN 3-Thienyl 392 CN 2-Furyl 393 CN 3-Furyl 394 CN1-Pyrrolyl 395 CN 1-Imidazolyl 396 CN 1,2,4-Triazolyl 397 CN1,3,4-Triazolyl 398 CN 4-Thiazolyl 399 CN 2-Benzothiazolyl 400 CN2-Pyridyloxy 401 CN 2-Pyrimidinyloxy 402 CN 2-Pyridylthio 403 CN2-Pyrimidinylthio 404 CN 2-Benzothiazolylthio 405 CN Phenylthiomethyl406 CN 2-Pyridylmethyl 407 CN 3-Pyridylmethyl 408 CN Furfuryloxy 409 CNThienylmethoxy 410 CN 3-Isoxazolylmethoxy 411 CN 2-Oxazolylmethoxy 412CN 2-Pyridylmethoxy 413 CN 2′-Furyl-2-ethenyl 414 CN2′-Thienyl-2-ethenyl 415 CN 3′-Pyridyl-2-ethenyl 416 CN Oxiranyl 417 CN1-Aziridinyl 418 CN 1-Azetidinyl 419 CN 1-Pyrrolidinyl 420 CN2-Tetrahydrofuryl 421 CN 2-Tetrahydropyranyl 422 CN 3-Tetrahydropyranyl423 CN 1-Piperidinyl 424 CN 1-Morpholinyl 425 CN 1-Piperazinyl 426 CN1,3-Dioxan-2-yl 427 CN 3-Tetrahydrothiopyranyl 428 CN2-Dihydropyranyloxy 429 CN 2-Tetrahydropyranyloxy oil; IR (film):12051131, 1087, 1047, 1004 430 CN (CH₂)₄ 431 CN (CH₂)₅ 432 CN (CH₂)₆ 433CN 434 CN 435 CN

435 CN

437 CN

438 CN

439 CN

440 CN

441 CN CF₃ 442 CN 2-Fluoroethyl 443 CN 2,2,2-Trifluoroethyl 444 CNPentafluoroethyl 445 CN Chloromethyl 446 CN Dichloromethyl 447 CNTrichloromethyl 448 CN 2-Chloroethyl 449 CN 2,2,2,-Trichloroethyl 450 CNPentachloroethyl 451 CN Cyclopropyl 452 CN Cyclobutyl 453 CN Cyclopentyl454 CN Cyclohexyl 455 CN 1-Methylcyclopropyl 456 CN2,2-Dimethylcyclopropyl 457 CN 1-Methylcyclohexyl 458 CN2,2-Difluorocyclopropyl 459 CN 2,2-Dichlorocyclopropyl 460 CN2,2-Dibromocyclopropyl 461 CN 2,2-Dichloro-3-methylcyclopropyl 462 CN2,2,3,3-Tetrafluorocyclobutyl 463 CN Ethenyl 464 CN 1-Propenyl 465 CN2-Methyl-1-propenyl 466 CN 4-Methylpent-3-en-1-yl 467 CN 2-Propenyl 468CN 2-Butenyl 469 CN 1-Methyl-2-propenyl 470 CN 3-Methyl-2-butenyl 471 CN2,2-Difluoroethenyl 472 CN 2,2-Dichloroethenyl 473 CN3,3,3-trifluoropropenyl 474 CN 3,3,3-trichloropropenyl 475 CN3-Chloro-2-propenyl 476 CN Cyclopent-1-enyl 477 CN Cyclopentadienyl 478CN Cyclohex-1-enyl 479 CN Pentafluorocyclopentadienyl 480 CNPentachlorocyclopentadienyl 481 CN Styryl 482 CH₃ Methoxymethyl 483 CH₃Ethoxymethyl 484 CH₃ m-Propoxymethyl 485 CH₃ iso-Propoxymethyl 486 CH₃tert.-Butoxymethyl 487 CH₃ 2-Methoxyprop-2-yl 488 CH₃ 2-Ethoxyprop-2-yl489 CH₃ 2-n-Propoxyprop-2-yl 490 CH₃ 2-iso-Propoxyprop-2-yl 491 CH₃2-tert.-Butoxyprop-2-yl 492 CH₃ Methylthiomethyl 493 CH₃tert.-Butylthiomethyl 494 CH₃ 2-Methylthiomethyl 495 CH₃2-iso-Propylthioprop-2-yl 496 CH₃ 2-tert.-Butylthioprop-2-yl 497 CH₃Methyl 498 CH₃ Ethyl 499 CH₃ n-Propyl 500 CH₃ iso-Propyl 501 CH₃ n-Butyl502 CH₃ iso-Butyl 503 CH₃ sec.-Butyl 504 CH₃ tert.-Butyl 505 CH₃ n-Hexyl506 CH₃ n-Decyl 507 CH₃ Cyclopropyl 508 CH₃ Cyclohexyl 509 CH₃Phenylthiomethyl 510 CH₃ 2-Phenylthiomethyl 511 CH₃2-(2′-Chlorophenylthio)prop-2-yl 512 CH₃ Ethynyl 513 CH₃ 1-Propynyl 514CH₃ Methoxy 515 CH₃ Ethoxy 516 CH₃ n-Propoxy 517 CH₃ iso-Propoxy 518 CH₃n-Butoxy 519 CH₃ iso-Butoxy 520 CH₃ sec.-Butoxy 521 CH₃ tert.-Butoxy 522CH₃ Methylthio 523 CH₃ Ethylthio 524 CH₃ n-Propylthio 525 CH₃iso-Propylthio 526 CH₃ n-Butylthio 527 CH₃ iso-Butylthio 528 CH₃sec.-Butylthio 529 CH₃ tert.-Butylthio 530 CH₃ Benzylthio 531 CH₃Trifluoromethoxy 532 CH₃ Cyano 533 CH₃ Amino 534 CH₃ Methylamino 535 CH₃Dimethylamino 536 CH₃ Ethylamino 537 CH₃ Diethylamino 538 CH₃Di-n-Propylamino 539 CH₃ Di-iso-Propylamino 540 CH₃ Di-n-Butylamino 541CH₃ Di-iso-Butylamino 542 CH₃ Acetyl 543 CH₃ Propion-1-yl 544 CH₃Butyr-1-yl 545 CH₃ iso-Butyr-1-yl 546 CH₃ Pivaloyl 547 CH₃ Benzoyl 548CH₃ 4-Chlorobenzoyl 549 CH₃ Benzylcarbonyl 550 CH₃ Methoxycarbonyl 551CH₃ Ethoxycarbonyl 552 CH₃ n-Propoxycarbonyl 553 CH₃ iso-Propoxycarbonyl554 CH₃ n-Butoxycarbonyl 555 CH₃ iso-Butoxycarbonyl 556 CH₃sec.-Butoxycarbonyl 557 CH₃ tert.-Butoxycarbonyl 558 CH₃n-Hexoxycarbonyl 559 CH₃ Phenoxycarbonyl 560 CH₃ 4-Chlorophenoxycarbonyl561 CH₃ Benzyloxycarbonyl 562 CH₃ Aminocarbonyl 563 CH₃Dimethylaminocarbonyl 564 CH₃ Diethylaminocarbonyl 565 CH₃Di-iso-Propylaminocarbonyl 566 CH₃ Phenylaminocarbonyl 567 CH₃N-Methyl-N-Phenylaminocarbonyl 568 CH₃ Phenyl 569 CH₃ 2-Fluorophenyloil; IR (film): 1708, 1634, 1257, 1129, 761 570 CH₃ 3-Fluorophenyl 571CH₃ 4-Fluorophenyl m.p.: 67-68° C.; IR(KBr): 1691, 1629, 1295, 1253,1132, 1037, 848 572 CH₃ Pentafluorophenyl 573 CH₃ 2-Chlorophenyl oil.: —574 CH₃ 3-Chlorophenyl 575 CH₃ 4-Chlorophenyl 576 CH₃ Pentachlorophenyl577 CH₃ 2,3-Dichlorophenyl 578 CH₃ 2,4-Dichlorophenyl oil; IR (film):1708, 1634, 1256, 1129 579 CH₃ 2,5-Dichlorophenyl m.p.: 80-2° C.;IR(KBr): 1704, 1634, 1250, 1132, 934, 766 580 CH₃ 2,6-Dichlorophenyl 581CH₃ 3,4-Dichlorophenyl 582 CH₃ 3,5-Dichlorophenyl m.p.: 87-88° C.; IR(KBr): 1699, 1303, 1071, 1015, 932, 835 583 CH₃ 2,3,4-Trichlorophenyloil; IR (film): 1709, 1627, 1257, 1131, 1109 584 CH₃2,3,5-Trichlorophenyl 585 CH₃ 2,3,6-Trichlorophenyl 586 CH₃2,4,5-Trichlorophenyl 587 CH₃ 2,4,6-Trichlorophenyl 588 CH₃3,4,6-Trichlorophenyl 589 CH₃ 2,3,4,6-Tetrachlorophenyl 590 CH₃2,3,5,6-Tetrachlorophenyl 591 CH₃ 2-Bromophenyl 592 CH₃ 3-Bromophenylm.p.: 60-2° C. IR (KBr): 1708, 1635, 1253, 1129, 1113, 933, 773 593 CH₃m.p.: 104-6° C.; IR(KBr): 1694, 1620, 1296, 1035, 938 594 CH₃2,4-Dibromophenyl 595 CH₃ 3-Bromo-4-Fluorophenyl 596 CH₃3-Bromo-4-Methoxyphenyl 597 CH₃ 2-Iodophenyl 598 CH₃ 3-Iodophenyl 599CH₃ 4-Iodophenyl 600 CH₃ 2-Chloro-4-fluorophenyl 601 CH₃2-Chloro-5-fluorophenyl 602 CH₃ 2-Chloro-6-fluorophenyl 603 CH₃2-Chloro-4-bromophenyl 604 CH₃ 2-Bromo-4-chlorophenyl 605 CH₃2-Bromo-4-fluorophenyl 606 CH₃ 3-Bromo-4-chlorophenyl 607 CH₃3-Chloro-4-fluorophenyl 608 CH₃ 3-Fluoro-4-chlorophenyl 609 CH₃2-Cyanophenyl 610 CH₃ 3-Cyanophenyl 611 CH₃ 4-Cyanophenyl 612 CH₃2-Nitrophenyl 613 CH₃ 3-Nitrophenyl 614 CH₃ 4-Nitrophenyl 615 CH₃2-Methylphenyl 616 CH₃ 3-Methylphenyl 617 CH₃ 4-Methylphenyl 618 CH₃2,4-Dimethylphenyl 619 CH₃ 2,6-Dimethylphenyl 620 CH₃ 3,4-Dimethylphenyl621 CH₃ 3,5-Dimethylphenyl 622 CH₃ 2,3,4-Trimethylphenyl 623 CH₃2,3,5-Trimethylphenyl 624 CH₃ 2,3,6-Trimethylphenyl 625 CH₃2,4,5-Trimethylphenyl 626 CH₃ 2,4,6-Trimethylphenyl 627 CH₃3,4,5-Trimethylphenyl 628 CH₃ Pentamethylphenyl 629 CH₃ 2-Ethylphenyl630 CH₃ 3-Ethylphenyl 631 CH₃ 4-Ethylphenyl 632 CH₃ 3,5-Diethylphenyl633 CH₃ 2-n-Propylphenyl 634 CH₃ 3-n-Propylphenyl 635 CH₃4-n-Propylphenyl 636 CH₃ 2-iso-Propylphenyl 637 CH₃ 3-iso-Propylphenyl638 CH₃ 4-iso-Propylphenyl 639 CH₃ 2,4-Di-iso-Propylphenyl 640 CH₃3,5-Di-iso-Propylphenyl 641 CH₃ 4-n-Butylphenyl 642 CH₃4-sec.-Butylphenyl 643 CH₃ 4-iso-Butylphenyl 644 CH₃ 4-tert.-Butylphenyl645 CH₃ 3-tert.-Butylphenyl 646 CH₃ 2-tert.-Butylphenyl 647 CH₃2,4-Di-tert.-Butylphenyl 648 CH₃ 3,5-Di-tert.-Butylphenyl 649 CH₃4-n-Hexylphenyl 650 CH₃ 4-n-Dodecylphenyl 651 CH₃2-Methyl-4-tert.-Butylphenyl 652 CH₃ 2-Methyl-6-tert.-Butylphenyl 653CH₃ 2-Methyl-4-iso-Propylphenyl 654 CH₃ 2-Methyl-4-Cyclohexylphenyl 655CH₃ 2-Methyl-4-Phenylphenyl 656 CH₃ 2-Methyl-4-Benzylphenyl 657 CH₃2-Methyl-4-Phenoxyphenyl 658 CH₃ 2-Methyl-4-Benzyloxyphenyl 659 CH₃2-Methyl-3-Chlorophenyl 660 CH₃ 2-Methyl-4-Chlorophenyl 661 CH₃2-Methyl-5-Chlorophenyl 662 CH₃ 2-Methyl-6-Chlorophenyl 663 CH₃2-Methyl-4-Fluorophenyl 664 CH₃ 2-Methyl-3-Bromophenyl 665 CH₃2-Methyl-4-Bromophenyl 666 CH₃ 2-Methyl-3-Methoxyphenyl 667 CH₃2-Methyl-4-Methoxyphenyl 668 CH₃ 2-Methyl-5-Methoxyphenyl 669 CH₃2-Methyl-6-methoxyphenyl 670 CH₃ 2-Methyl-4-iso-Propoxyphenyl 671 CH₃2-Methyl-2,5-Dimethoxyphenyl 672 CH₃ 2-Methoxyphenyl oil: IR (film):1708, 1634, 1285, 1256, 1129, 1111 673 CH₃ 3-Methoxyphenyl oil: IR(film): 1708, 1253, 1129 674 CH₃ 4-Methoxyphenyl 675 CH₃2,3-Dimethoxyphenyl 676 CH₃ 2,4-Dimethoxyphenyl 677 CH₃2,5-Dimethoxyphenyl 678 CH₃ 2,6-Dimethoxyphenyl 679 CH₃3,4-Dimethoxyphenyl 680 CH₃ 3,5-Dimethoxyphenyl 681 CH₃3,6-Dimethoxyphenyl 682 CH₃ 2,3,4-Trimethoxyphenyl 683 CH₃2,3,5-Trimethoxyphenyl 684 CH₃ 2,3,6-Trimethoxyphenyl 685 CH₃2,4,5-Trimethoxyphenyl 686 CH₃ 2,4,6-Trimethoxyphenyl 687 CH₃3,4,5-Trimethoxyphenyl 688 CH₃ 2-Ethoxyphenyl 689 CH₃ 3-Ethoxyphenyl 690CH₃ 4-Ethoxyphenyl 691 CH₃ 2-iso-Propoxyphenyl 692 CH₃3-iso-Propoxyphenyl 693 CH₃ 4-iso-Propoxyphenyl 694 CH₃3-tert.-Butoxyphenyl 695 CH₃ 4-tert.-Butoxyphenyl 696 CH₃2-Trifluoromethoxyphenyl 697 CH₃ 3-Trifluoromethoxyphenyl 698 CH₃4-Trifluoromethoxyphenyl 699 CH₃ 3-(1′, 1′,2′,2′-Tetrafluoro)ethoxyphenyl 700 CH₃ 4-(1′, 1′,2′,2′-Tetrafluoro)ethoxyphenyl 701 CH₃ 2-Chloromethylphenyl 702 CH₃3-Chloromethylphenyl 703 CH₃ 4-Chloromethylphenyl 704 CH₃2-Trifluoromethylphenyl oil: IR (film): 1705, 1634, 1313, 1130, 1107,767 705 CH₃ 3-Trifluoromethylphenyl oil: IR (film): 1710, 1635, 1276,1128 706 CH₃ 4-Trifluoromethylphenyl m.p.: 104-5° C.; IR (KBr): 1697,1628 1323, 1123 707 CH₃ 2-(Methoxyiminomethyl)phenyl 708 CH₃3-(Methoxyiminomethyl)phenyl 709 CH₃ 4-(Methoxyiminomethyl)phenyl 710CH₃ 2-(Ethoxyiminomethyl)phenyl 711 CH₃ 3-(Ethoxyiminomethyl)phenyl 712CH₃ 4-(Ethoxyiminomethyl)phenyl 713 CH₃ 2-(n-Propoxyiminomethyl)phenyl714 CH₃ 3-(n-Propoxyiminomethyl)phenyl 715 CH₃4-(n-Propoxyiminoniethyl)phenyl 716 CH₃ 2-(iso-Propoxyiminomethyl)phenyl717 CH₃ 3-(iso-Propoxyiminomethyl)phenyl 718 CH₃4-(iso-Propoxyiminomethyl)phenyl 719 CH₃ 2-(n-Butoxyiminomethyl)phenyl720 CH₃ 3-(n-Butoxyiminomethyl)phenyl 721 CH₃4-(n-Butoxyiminomethyl)phenyl 722 CH₃ 2-(iso-Butoxyiminomethyl)phenyl723 CH₃ 3-(iso-Butoxyiminomethyl)phenyl 724 CH₃4-(iso-Butoxyiminomethyl)phenyl 725 CH₃2-(tert.-Butoxyiminomethyl)phenyl 726 CH₃3-(tert.-Butoxyiminomethyl)phenyl 727 CH₃4-(tert.-Butoxyiminomethyl)phenyl 728 CH₃ 2-(n-Pentoxyiminomethyl)phenyl729 CH₃ 3-(n-Pentoxyiminomethyl)phenyl 730 CH₃4-(n-Pentoxyiminomethyl)phenyl 731 CH₃ 2-(n-Hextoxyiminomethyl)phenyl732 CH₃ 3-(n-Hextoxyiminomethyl)phenyl 733 CH₃4-(n-Hextoxyiminomethyl)phenyl 734 CH₃ 2-(Allyloxyiminomethyl)phenyl 735CH₃ 3-(Allyloxyiminomethyl)phenyl 736 CH₃ 4-(Allyloxyiminomethyl)phenyl737 CH₃ 2-(Benzyloxyiminomethyl)phenyl 738 CH₃3-(Benzyloxyiminomethyl)phenyl 739 CH₃ 4-(Benzyloxyiminomethyl)phenyl740 CH₃ 2-(Methoxyimino(1′-ethyl)phenyl 741 CH₃3-(Methoxyimino(1′-ethyl)phenyl 742 CH₃ 4-(Methoxyimino(1′-ethyl)phenyl743 CH₃ 2-(Ethoxyimino(1′-ethyl)phenyl 744 CH₃3-(Ethoxyimino(1′-ethyl)phenyl 745 CH₃ 4-(Ethoxyimino(1′-ethyl)phenyl746 CH₃ 2-(n-Propoxyimino(1′-ethyl)phenyl 747 CH₃3-(n-Propoxyimino(1′-ethyl)phenyl 748 CH₃4-(n-Propoxyimino(1′-ethyl)phenyl 749 CH₃2-(n-Butoxyimino(1′-ethyl)phenyl 750 CH₃3-(n-Butoxyimino(1′-ethyl)phenyl 751 CH₃4-(n-Butoxyimino(1′-ethyl)phenyl 752 CH₃2-(n-Pentoxyimino(1′-ethyl)phenyl 753 CH₃3-(n-Pentoxyimino(1′-ethyl)phenyl 754 CH₃4-(n-Pentoxyimino(1′-ethyl)phenyl 755 CH₃2-(n-Hexoxyimino(1′-ethyl)phenyl 756 CH₃3-(n-Hexoxyimino(1′-ethyl)phenyl 757 CH₃4-(n-Hexoxyimino(1′-ethyl)phenyl 758 CH₃2-(n-Allyloxyimino(1′-ethyl)phenyl 759 CH₃3-(n-Allyloxyimino(1′-ethyl)phenyl 760 CH₃4-(n-Allyloxyimino(1′-ethyl)phenyl 761 CH₃2-(n-Benzyloxyimino(1′-ethyl)phenyl 762 CH₃3-(n-Benzyloxyimino(1′-ethyl)phenyl 763 CH₃4-(n-Benzyloxyimino(1′-ethyl)phenyl 764 CH₃ 2-Phenylphenyl 765 CH₃3-Phenylphenyl 766 CH₃ 4-Phenylphenyl 767 CH₃ 2-Phenoxyphenyl 768 CH₃3-Phenoxyphenyl 769 CH₃ 4-Phenoxyphenyl oil; IR (film): 1708, 1489,1240, 1129 770 CH₃ 2-Benzoxyphenyl 771 CH₃ 3-Benzoxyphenyl 772 CH₃4-Benzoxyphenyl 773 CH₃ 4-(Imidazol-1′-yl)phenyl 774 CH₃4-(Piperazin-1′-yl)phenyl 775 CH₃ 4-(Morpholin-1′-yl)phenyl 776 CH₃4-(Piperadin-1′-yl)phenyl 777 CH₃ 4-(Piperidyl-2′-oxy)phenyl 778 CH₃2-Cyclopropylphenyl 779 CH₃ 3-Cyclopropylphenyl 780 CH₃4-Cyclopropylphenyl 781 CH₃ 3-Cyclohexylphenyl 782 CH₃4-Cyclohexylphenyl 783 CH₃ 4-Oxiranylphenyl 784 CH₃ 4-(1-40 ,3-40-Dioxan-2′yl)phenyl 785 CH₃ 4-(Tetrahydropyran-2-yloxy)phenyl 786 CH₃1-Naphthyl 787 CH₃ 2-Naphthyl 788 CH₃ 9-Anthryl 789 CH₃ 1-Naphtoxy 790CH₃ 2-Naphtoxy 791 CH₃ 9-Anthroxy 792 CH₃ Phenoxy 793 CH₃2-Chlorophenoxy 794 CH₃ 3-Chlorophenoxy 795 CH₃ 4-Chlorophenoxy 796 CH₃4-Methylphenoxy 797 CH₃ 4-tert.-Butylphenoxy 798 CH₃ 4-Methoxyphenoxy799 CH₃ 4-Ethoxyphenoxy 800 CH₃ 4-tert.-Butoxyphenoxy 801 CH₃ Phenylthio802 CH₃ 2-Chlorophenylthio 803 CH₃ 4-Chlorophenylthio 804 CH₃ Benzyl 805CH₃ 2-Methylbenzyl 806 CH₃ 3-Methylbenzyl 807 CH₃ 4-Methylbenzyl 808 CH₃4-tert.-Butylbenzyl 809 CH₃ 2-Chlorobenzyl 810 CH₃ 3-Chlorobenzyl 811CH₃ 4-Chlorobenzyl 812 CH₃ 2,4-Dichlorobenzyl 813 CH₃ 2,6-Dichlorobenzyl814 CH₃ 2,4,6-Trichlorobenzyl 815 CH₃ 2-Trifluoromethylbenzyl 816 CH₃3-Trifluoromethylbenzyl 817 CH₃ 4-Trifluoromethylbenzyl 818 CH₃2-Methoxybenzy 819 CH₃ 4-Methoxybenzy 820 CH₃ 4-tert.-Butoxybenzyl 821CH₃ 4-Phenoxybenzyl 822 CH₃ 1-Phenethyl 823 CH₃ 1-Phenylpropyl 824 CH₃1-Phenethyl 825 CH₃ 2-Phenethyl 826 CH₃ 3-Phenethyl 827 CH₃2-Methyl-2-phenylpropyl 828 CH₃ 2-Methyl-3-phenylpropyl 829 CH₃4-Phenylbutyl 830 CH₃ 2-Phenyl-1-ethenyl 831 CH₃ 1-Phenyl-1-ethenyl 832CH₃ 1-Phenyl-1-propenyl 833 CH₃ 1-Phenyl-1-propen-2-yl 834 CH₃2,2-Diphenylethenyl 835 CH₃ Phenoxymethyl 836 CH₃ 2-Pyridyl 837 CH₃3-Pyridyl 838 CH₃ 4-Pyridyl 839 CH₃ 2,6-Pyrimidinyl 840 CH₃1,5-Pyrimidinyl 841 CH₃ 2-Thienyl 842 CH₃ 3-Thienyl 843 CH₃ 2-Furyl 844CH₃ 3-Furyl 845 CH₃ 1-Pyrrolyl 846 CH₃ 1-Imidazolyl 847 CH₃1,2,4-Triazolyl 848 CH₃ 1,3,4-Triazolyl 849 CH₃ 4-Thiazolyl 850 CH₃2-Benzothiazolyl 851 CH₃ 2-Pyridyloxy 852 CH₃ 2-Pyrimidinyloxy 853 CH₃2-Pyridylthio 854 CH₃ 2-Pyrimidinylthio 855 CH₃ 2-Benzothiazolylthio 856CH₃ Phenylthiomethyl 857 CH₃ 2-Pyridylmethyl 858 CH₃ 3-Pyridylmethyl 859CH₃ Furfuryloxy 860 CH₃ Thienylmethoxy 861 CH₃ 3-Isoxazolylmethoxy 862CH₃ 2-Oxazolylmethoxy 863 CH₃ 2-Pyridylmethoxy 864 CH₃2′-Furyl-2-ethenyl 865 CH₃ 2′-Thienyl-2-ethenyl 866 CH₃3′-Pyridyl-2-ethenyl 867 CH₃ Oxiranyl 868 CH₃ 1-Aziridinyl 869 CH₃1-Azetidinyl 870 CH₃ 1-Pyrrolidinyl 871 CH₃ 2-Tetrahydrofuryl 872 CH₃2-Tetrahydropyranyl 873 CH₃ 3-Tetrahydropyranyl 874 CH₃ 1-Piperidinyl875 CH₃ 1-Morpholinyl 876 CH₃ 1-Piperazinyl 877 CH₃ 1,3-Dioxan-2-yl 878CH₃ 3-Tetrahydrothiopyranyl 879 CH₃ 2-Dihydropyranyloxy 880 CH₃2-Tetrahydropyranyloxy 881 CH₃ CF₃ 882 CH₃ 2-Fluoroethyl 883 CH₃2,2,2-Trifluoroethyl 884 CH₃ Pentafluoroethyl 885 CH₃ Chloromethyl 886CH₃ Dichloromethyl 887 CH₃ Trichloromethyl 888 CH₃ 2-Chloroethyl 889 CH₃2,2,2,-Trichloroethyl 890 CH₃ Pentachloroethyl 891 CH₃ Cyclopropyl 892CH₃ Cyclobutyl 893 CH₃ Cyclopentyl 894 CH₃ Cyclohexyl 895 CH₃1-Methylcyclopropyl 896 CH₃ 2,2-Dimethylcyclopropyl 897 CH₃1-Methylcyclohexyl 898 CH₃ 2,2-Difluorocyclopropyl 899 CH₃2,2-Dichlorocyclopropyl 900 CH₃ 2,2-Dibromocyclopropyl 901 CH₃2,2-Dichloro-3-methylcyclopropyl 902 CH₃ 2,2,3,3-Tetrafluorocyclobutyl903 CH₃ Ethenyl 904 CH₃ 1-Propenyl 905 CH₃ 2-Methyl-1-propenyl 906 CH₃4-Methylpent-3-en-1-yl 907 CH₃ 2-Propenyl 908 CH₃ 2-Butenyl 909 CH₃1-Methyl-2-propenyl 910 CH₃ 3-Methyl-2-butenyl 911 CH₃2,2-Difluoroethenyl 912 CH₃ 2,2-Dichloroethenyl 913 CH₃3,3,3-trifluoropropenyl 914 CH₃ 3,3,3-trichloropropenyl 915 CH₃3-Chloro-2-propenyl 916 CH₃ Cyclopent-1-enyl 917 CH₃ Cyclopentadienyl918 CH₃ Cyclohex-1-enyl 919 CH₃ Pentafluorocyclopentadienyl 920 CH₃Pentachlorocyclopentadienyl 921 Phenyl Phenyl 922 Phenyl 2-Fluorophenyl923 Phenyl 4-Fluorophenyl 924 Phenyl 2-Chlorophenyl 925 Phenyl3-Chlorophenyl 926 Phenyl 4-Chlorophenyl 927 Phenyl 3,4-Dichlorophenyl928 Phenyl 4-Nitrophenyl 929 Phenyl 2-CF₃-Phenyl 930 Phenyl 3-CF₃-Phenyl931 Phenyl 4-CF₃-Phenyl 932 Phenyl 2-Methylphenyl 933 Phenyl3-Methylphenyl 934 Phenyl 4-Methylphenyl 935 Phenyl 2,4-Dimethylphenyl936 Phenyl 4-tert.-Butylphenyl 937 Phenyl 4-Methoxyphenyl 9384-Fluorophenyl 4-Fluorophenyl 939 2-Fluorophenyl 4-Fluorophenyl 9402-Chlorophenyl 4-Fluorophenyl 941 2-Chlorophenyl 2-Chlorophenyl 9423-Chlorophenyl 3-Chlorophenyl 943 4-Chlorophenyl 4-Chlorophenyl 9442-Chlorophenyl 4-Chlorophenyl 945 4-Methoxyphenyl 4-Methoxyphenyl 9464-Dimethylaminophenyl 4-Dimethylaminophenyl 947 Phenyl Naphthyl 948Ethyl Ethyl 949 Ethyl n-Propyl 950 Ethyl iso-Propyl 951 Ethyl n-Butyl952 Ethyl iso-Butyl 953 Ethyl 2-Methyl-butyl 954 Ethyl Benzyl 955n-Propyl n-Propyl 956 iso-Propyl iso-Propyl 957 n-Butyl n-Butyl 958iso-Butyl iso-Butyl 959 tert.-Butyl tert.-Butyl 960 Benzyl Benzyl 961Pentachloroethyl Pentachloroethyl 962 n-Hexyl n-Hexyl 963 EthoxycarbonylEthoxycarbonyl 964 Phenyl Benzoyl 965 Ethyl Phenyl 966 n-Butyl Phenyl967 Styryl Styryl 968 2-Pyridyl 2-Pyridyl 969 3-Pyridyl 3-Pyridyl 970CH₃ 3,4-Dibenzyloxyphenyl IR (film): 1707, 1581, 1256, 1157, 1129

TABLE II

No. R³ R⁴ Data 1 Cl Phenyl 2 Cl Cyano 3 Cl Ethoxycarbonyl 4 ClCyclopropyl 5 CF₃ CF₃ 6 CF₃ Phenyl 7 CCl₃ CCl₃ 8 CCl₃ Phenyl 9 CH₂ClPhenyl 10 CF₂CF₃ Phenyl 11 CF₂Cl Phenyl 12 CHCl₂ Phenyl 13 CyclopropylCyclopropyl 14 Cyclopropyl Phenyl oil; IR (film): 1437, 1321, 1219,1045, 983, 766 15 Cyclopropyl 4-Fluorophenyl oil; IR (film): 1508, 1321,1222, 1046, 985, 839 16 Cyclopropyl 4-Chlorophenyl oil; IR (film): 1489,1321, 1218, 1090, 1046, 829 17 Cyclopropyl 4-Methoxyphenyl oil; IR(film): 1300, 1250, 1218, 983, 833 18 Cyclopropyl 4-Ethoxyphenyl 19Cyclopropyl 4-Phenoxyphenyl 20 Cyclopropyl Pentachlorophenyl 21Cyclopropyl Pentafluorophenyl 22 Cyclopentyl Phenyl 23 Cyclohexyl Phenyl24 Phenyl 2,2-Dichloro-1-methylcyclopropyl 25 Phenyl2,2-Difluorocyclopropyl 26 Phenyl 2,2-Dichlorocyclopropyl 27 Phenyl2,2-Dibromocyclopropyl 28 Phenyl 2,2,3,3-Tetrafluorocyclobutyl 29 Phenyl2,2-Dimethylcyclopropyl 30 Phenyl 1-Methylcyclohexyl 31 CN Methoxymethyl32 CN Ethoxymethyl 33 CN n-Propoxymethyl 34 CN iso-Propoxymethyl 35 CNtert.-Butoxymethyl 36 CN 2-Methoxyprop-2-yl m.p.: 83° C.; IR (KBr):1437.1223, 1206, 1069, 1006 37 CN 2-Ethoxyprop-2-yl oil; IR (film):1439, 3122, 1221, 1202, 1048 38 CN 2-n-Propoxyprop-2-yl oil; IR (film):1438, 1322, 1221, 1203, 1048 39 CN 2-iso-Propoxyprop-2-yI m.p.: 74-5° C.IR (KBr): 1302, 1231, 1169, 1108, 1079, 997, 757 40 CN2-tert.-Butoxyprop-2-yl 41 CN Methylthiomethyl 42 CNtert.-Butylthiomethyl 43 CN 2-Methylthioprop-2-yl m.p.: 107° C.; IR(KBr): 1434, 1297, 1126, 1066, 1010, 769 44 CN 2-iso-Propylthioprop-2-yloil; IR (film): 1438, 1366, 1321, 1221, 1202 45 CN2-tert.-Butylthioprop-2-yl 46 CN Methyl 47 CN Ethyl 48 CN n-Propyl 49 CNiso-Propyl oil; IR (film): 1439, 1321, 1222, 1012, 767 50 CN n-Butyl 51CN iso-Butyl 52 CN sec.-Butyl 53 CN tert.-Butyl 54 CN n-Hexyl 55 CNn-Decyl 56 CN Cyclopropyl m.p.: 74-75° C.; IR (KBr): 1433, 1223, 1043,763 57 CN Cyclohexyl 58 CN Phenylthiomethyl 59 CN 2-Phenylthiomethyl 60CN 2-(2′-Chlorophenylthio)prop-2-yl 61 CN Ethynyl 62 CN 1-Propynyl 63 CNMethoxy 64 CN Ethoxy 65 CN n-Propoxy 66 CN iso-Propoxy 67 CN n-Butoxy 68CN iso-Butoxy 69 CN sec.-Butoxy 70 CN tert.-Butoxy 71 CN Methylthio 72CN Ethylthio 73 CN n-Propylthio 74 CN iso-Propylthio 75 CN n-Butylthio76 CN iso-Butylthio 77 CN sec.-Butylthio 78 CN tert.-Butylthio 79 CNBenzylthio 80 CN Trifluoromethoxy 81 CN Cyano 82 CN Amino 83 CNMethylamino 84 CN Dimethylamino 85 CN Ethylamino 86 CN Diethylamino 87CN Di-n-Propylamino 88 CN Di-iso-Propylamino 89 CN Di-n-Butylamino 90 CNDi-iso-Butylamino 91 CN Acetyl 92 CN Propion-1-yl 93 CN Butyr-1-yl 94 CNiso-Butyl-1-yl 95 CN Pivaloyl 96 CN Benzoyl 97 CN 4-Chlorobenzoyl 98 CNBenzylcarbonyl 99 CN Methoxycarbonyl 100 CN Ethoxycarbonyl 101 CNn-Propoxycarbonyl 102 CN iso-Propoxycarbonyl 103 CN n-Butoxycarbonyl 104CN iso-Butoxycarbonyl 105 CN sec.-Butoxycarbonyl 106 CNtert.-Butoxycarbonyl 107 CN n-Hexoxycarbonyl 108 CN Phenoxycarbonyl 109CN 4-Chlorophenoxycarbonyl 110 CN Benzyloxycarbonyl 111 CN Aminocarbonyl112 CN Dimethylaminocarbonyl 113 CN Diethylaminocarbonyl 114 CNDi-iso-Propylaminocarbonyl 115 CN Phenylaminocarbonyl 116 CNN-Methyl-N-phenylaminocarbonyl 117 CN Phenyl m.p.: 99-100° C.; IR (KBr):1436, 1215, 1208, 1097, 1026, 944, 766, 690 118 CN 2-Fluorophenyl 119 CN3-FluorophenyI 120 CN 4-Fluorophenyl 121 CN Pentafluorophenyl 122 CN2-Chlorophenyl 123 CN 3-Chlorophenyl 124 CN 4-Chlorophenyl 125 CNPentachlorophenyl 126 CN 2,3-Dichlorophenyl 127 CN 2,4-Dichlorophenyl128 CN 2,5-Dichlorophenyl 129 CN 2,6-Dichlorophenyl 130 CN3,4-Dichlorophenyl 131 CN 3,5-Dichlorophenyl 132 CN2,3,4-Trichlorophenyl 133 CN 2,3,5-Trichlorophenyl 134 CN2,3,6-Trichlorophenyl 135 CN 2,4,5-Trichlorophenyl 136 CN2,4,6-Trichlorophenyl 137 CN 3,4,5-Trichlorophenyl 138 CN2,3,4,6-Tetrachlorophenyl 139 CN 2,3,5-6-Tetrachlorophenyl 140 CN2-Bromophenyl 141 CN 3-Bromophenyl 142 CN 4-Bromophenyl 143 CN2,4-Dibromophenyl 144 CN 3-Bromo-4-fluorophenyl 145 CN3-Bromo-4-methoxyphenyl 146 CN 2-Iodophenyl 147 CN 3-Iodophenyl 148 CN4-Iodophenyl 149 CN 2-Chloro-4-fluorophenyl 150 CN2-Chloro-5-fluorophenyl 151 CN 2-Chloro-6-fluorophenyl 152 CN2-Chloro-4-bromophenyl 153 CN 2-Bromo-4-chlorophenyl 154 CN2-Bromo-4-fluorophenyl 155 CN 3-Bromo-4-chlorophenyl 156 CN3-Chloro-4-fluorophenyl 157 CN 3-Fluoro-4-chlorophenyl 158 CN2-Cyanophenyl 159 CN 3-Cyanophenyl 160 CN 4-Cyanophenyl 161 CN2-Nitrophenyl 162 CN 3-Nitrophenyl 163 CN 4-Nitrophenyl 164 CN2-Methylphenyl 165 CN 3-Methylphenyl 166 CN 4-Methylphenyl 167 CN2,4-Dimethylphenyl 168 CN 2,6-Dimethylphenyl 169 CN 3,4-Dimethylphenyl170 CN 3,5-Dimethylphenyl 171 CN 2,3,4-Trimethylphenyl 172 CN2,3,5-Trimethylphenyl 173 CN 2,3,6-Trimethylphenyl 174 CN2,4,5-Trimethylphenyl 175 CN 2,4,6-Trimethylphenyl 176 CN3,4,5-Trimethylphenyl 177 CN Pentamethylphenyl 178 CN 2-Ethylphenyl 179CN 3-Ethylphenyl 180 CN 4-Ethylphenyl 181 CN 3,5-Diethylphenyl 182 CN2-n-Propylphenyl 183 CN 3-n-Propylphenyl 184 CN 4-n-Propylphenyl 185 CN2-iso-Propylphenyl 186 CN 3-iso-Propylphenyl 187 CN 4-iso-Propylphenyl188 CN 2,4-Di-iso-Propylphenyl 189 CN 3,5-Di-iso-Propylphenyl 190 CN4-n-Butylphenyl 191 CN 4-sec.-Butylphenyl 192 CN 4-iso-Butylphenyl 193CN 4-tert.-Butylphenyl 194 CN 3-tert.-Butylphenyl 195 CN2-tert.-Butylphenyl 196 CN 2,4-Di-tert.-Butylphenyl 197 CN3,5-Di-tert.-Butylphenyl 198 CN 4-n-Hexylphenyl 199 CN 4-n-Dodecylphenyl200 CN 2-Methyl-4-tert.-Butylphenyl 201 CN 2-Methyl-6-tert.-Butylphenyl202 CN 2-Methyl-4-iso-Propylphenyl 203 CN 2-Methyl-4-Cyclohexylphenyl204 CN 2-Methyl-4-Phenylphenyl 205 CN 2-Methyl-4-Benzylphenyl 206 CN2-Methyl-4-Phenoxyphenyl 207 CN 2-Methyl-4-Benzyloxyphenyl 208 CN2-Methyl-3-Chlorophenyl 209 CN 2-Methyl-4-Chlorophenyl 210 CN2-Methyl-5-Chlorophenyl 211 CN 2-Methyl-6-Chlorophenyl 212 CN2-Methyl-4-Fluorophenyl 213 CN 2-Methyl-3-Bromophnyl 214 CN2-Methyl-4-Bromophenyl 215 CN 2-Methyl-3-Methoxyphenyl 216 CN2-Methyl-4-Methoxyphenyl 217 CN 2-Methyl-5-Methoxyphenyl 218 CN2-Methyl-6-Methoxyphenyl 219 CN 2-Methyl-4-iso-Propoxyphenyl 220 CN2-Methyl-2,5-Dimethoxyphenyl 221 CN 2-Methoxyphenyl 222 CN3-Methoxyphenyl 223 CN 4-Methoxyphenyl 224 CN 2,3-Dimethoxyphenyl 225 CN2,4-Dimethoxyphenyl 226 CN 2,5-Dimethoxyphenyl 227 CN2,6-Dimethoxyphenyl 228 CN 3,4-Dimethoxyphenyl 229 CN3,5-Dimethoxyphenyl 230 CN 3,6-Dimethoxyphenyl 231 CN2,3,4-Trimethoxyphenyl 232 CN 2,3,5-Trimethoxyphenyl 233 CN2,3,6-Trimethoxyphenyl 234 CN 2,4,5-Trimethoxyphenyl 235 CN2,4,6-Trimethoxyphenyl 236 CN 3,4,5-Trimethoxyphenyl 237 CN2-Ethoxyphenyl 238 CN 3-Ethoxyphenyl 239 CN 4-Ethoxyphenyl 240 CN2-iso-Propoxyphenyl 241 CN 3-iso-Propoxyphenyl 242 CN4-iso-Propoxyphenyl 243 CN 3-tert.-Butoxyphenyl 244 CN4-tert.-Butoxyphenyl 245 CN 2-Trifluoromethoxyphenyl 246 CN3-Trifluoromethoxyphenyl 247 CN 4-Trifluoromethoxyphenyl 248 CN3-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl 249 CN4-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl 250 CN 2-Chloromethylphenyl 251CN 3-Chloromethylphenyl 252 CN 4-Chloromethylphenyl 253 CN2-Trifluoromethylphenyl 254 CN 3-Trifluoromethylphenyl 255 CN4-Trifluoromethylphenyl 256 CN 2-(Methoxyiminomethyl)phenyl 257 CN3-(Methoxyiminomethyl)phenyl 258 CN 4-(Methoxyiminomethyl)phenyl 259 CN2-(Ethoxyiminomethyl)phenyl 260 CN 3-(Ethoxyiminomethyl)phenyl 261 CN4-(Ethoxyiminomethyl)phenyl 262 CN 2-(n-Propoxyiminomethyl)phenyl 263 CN3-(n-Propoxyiminomethyl)phenyl 264 CN 4-(n-Propoxyiminomethyl)phenyl 265CN 2-(iso-Propoxyiminomethyl)phenyl 266 CN3-(iso-Propoxyiminomethyl)phenyl 267 CN 4-(iso-Propoxyiminomethyl)phenyl268 CN 2-(n-Butoxyiminomethyl)phenyl 269 CN3-(n-Butoxyiminomethyl)phenyl 270 CN 4-(n-Butoxyiminomethyl)phenyl 271CN 2-(iso-Butoxyiminomethyl)phenyl 272 CN3-(iso-Butoxyiminomethyl)phenyl 273 CN 4-(iso-Butoxyiminomethyl)phenyl274 CN 2-(tert.-Butoxyiminomethyl)phenyl 275 CN3-(tert.-Butoxyiminomethyl)phenyl 276 CN4-(tert.-Butoxyiminomethyl)phenyl 277 CN 2-(n-Pentoxyiminomethyl)phenyl278 CN 3-(n-Pentoxyiminomethyl)phenyl 279 CN4-(n-Pentoxyiminomethyl)phenyl 280 CN 2-(n-Hexooxyiminomethyl)phenyl 281CN 3-(n-Hexoxyiminomethyl)phenyl 282 CN 4-(n-Hexoxyiminomethyl)phenyl283 CN 4-(n-Hexoxyiminomethyl)phenyl 284 CN3-(Allyloxyiminomethyl)phenyl 285 CN 4-(Allyloxyiminomethyl)phenyl 286CN 2-(Benzyloxyiminomethyl)phenyl 287 CN 3-(Benzyloxyiminomethyl)phenyl288 CN 4-(Benzyloxyiminomethyl)phenyl 289 CN2-(Methoxyimino-1′-ethyl)phenyl 290 CN 3-(Methoxyimino-1′-ethyl)phenyl291 CN 4-(Methoxyimino-1′-ethyl)phenyl 292 CN2-(Ethoxyimino-1′-ethyl)phenyl 293 CN 3-(Ethoxyimino-1′-ethyl)phenyl 294CN 4-(Ethoxyimino-1′-ethyl)phenyl 295 CN2-(n-Propoxyimino-1′-ethyl)phenyl 296 CN3-(n-Propoxyimino-1′-ethyl)phenyl 297 CN4-(n-Propoxyimino-1′-ethyl)phenyl 298 CN2-(n-Butoxyamino-1′-ethyl)phenyl 299 CN 3-(n-Butoxyamino-1′-ethyl)phenyl300 CN 4-(n-Butoxyamino-1′-ethyl)phenyl 301 CN2-(n-Pentoxyimino-1′-ethyl)phenyl 302 CN3-(n-Pentoxyimino-1′-ethyl)phenyl 303 CN4-(n-Pentoxyimino-1′-ethyl)phenyl 304 CN2-(n-Hexoxyimino-1′-ethyl)phenyl 305 CN 3-(n-Hexoxyimino-1′-ethyl)phenyl306 CN 4-(n-Hexoxyimino-1′-ethyl)phenyl 307 CN2-(Allyloxyimino-1′-ethyl)phenyl 308 CN 3-(Allyloxyimino-1′-ethyl)phenyl309 CN 4-(Allyloxyimino-1′-ethyl)phenyl 310 CN2-(Benzyloxyimino-1′-ethyl)phenyl 311 CN3-(Benzyloxyimino-1′-ethyl)phenyl 312 CN4-(Benzyloxyimino-1′-ethyl)phenyl 313 CN 2-Phenylphenyl 314 CN3-Phenylphenyl 315 CN 4-Phenylphenyl 316 CN 2-Phenoxyphenyl 317 CN3-Phenoxyphenyl 318 CN 4-Phenoxyphenyl 319 CN 2-Benzyloxyphenyl 320 CN3-Benzyloxyphenyl 321 CN 4-Benzyloxyphenyl 322 CN4-(Imidazol-1′-yl)phenyl 323 CN 4-(Piperazin-1′-yl)phenyl 324 CN4-(Morpholin-1′-yl)phenyl 325 CN 4-(Piperidin-1′-yl)phenyl 326 CN4-(Pyridyl-2′-oxy)phenyl 327 CN 2-Cyclopropylphenyl 328 CN3-Cyclopropylphenyl 329 CN 4-Cyclopropylphenyl 330 CN 3-Cyclohexylphenyl331 CN 4-Cyclohexylphenyl 332 CN 4-Oxiranylphenyl 333 CN4-(1′,3′-Dioxan-2′-yl)phenyl 334 CN 4-(Tetrahydropyran-2-yloxy)phenyl335 CN 1-Naphthyl 336 CN 2-Naphthyl 337 CN 9-Anthryl 338 CN 1-Naphthoxy339 CN 2-Naphthoxy 340 CN 9-Anthroxy 341 CN Phenoxy 342 CN2-Chlorophenoxy 343 CN 3-Chlorophenoxy 344 CN 4-Chlorophenoxy 345 CN4-Methylphenoxy 346 CN 4-tert.-Butylphenoxy 347 CN 4-Methoxyphenoxy 348CN 4-Ethoxyphenoxy 349 CN 4-tert.-Butoxyphenoxy 350 CN Phenylthio 351 CN2-Chlorophenylthio 352 CN 4-Chlorophenylthio 353 CN Benzyl 354 CN2-Methylbenzyl 355 CN 3-Methylbenzyl 356 CN 4-Methylbenyzl 357 CN4-tert.-Butylbenzyl 358 CN 2-Chlorobenzyl 359 CN 3-Chlorobenzyl 360 CN4-Chlorobenzyl 361 CN 2,4-Dichlorobenzyl 362 CN 2,6-Dichlorobenzyl 363CN 2,4,6-Trichlorobenzyl 364 CN 2-Trifluoromethylbenzyl 365 CN3-Trifluoromethylbenzyl 366 CN 4-Trifluoromethylbenzyl 367 CN2-Methoxybenzyl 368 CN 4-Methoxybenzyl 369 CN 4-tert.-Butoxybenzyl 370CN 4-Phenoxybenzyl 371 CN 1-Phenethyl 372 CN 2-Phenethyl 373 CN1-Phenylpropyl 374 CN 2-Phenylpropyl 375 CN 3-Phenylpropyl 376 CN2-Methyl-2-phenylpropyl 377 CN 2-Methyl-3-phenylpropyl 378 CN4-Phenylbutyl 379 CN 2-Phenyl-1-ethenyl 380 CN I-Phenyl-1-ethenyl 381 CN1-Phenyl-1-propenyl 382 CN 1-Phenyl-1-propen-2-yl 383 CN2,2-Diphenylethenyl 384 CN Phenoxymethyl 385 CN 2-Pyridyl 386 CN3-Pyridyl 387 CN 4-Pyridyl 388 CN 2,6-Pyrimidinyl 389 CN 1,5-Pyrimidinyl390 CN 2-Thienyl 391 CN 3-Thienyl 392 CN 2-Furyl 393 CN 3-Furyl 394 CN1-Pyrrolyl 395 CN 1-Imidazolyl 396 CN 1,2,3-Triazolyl 397 CN1,3,4-Triazolyl 398 CN 4-Thiazolyl 399 CN 2-Benzothiazolyl 400 CN2-Pyridyloxy 401 CN 2-Pyrimidinyloxy 402 CN 2-Pyridylthio 403 CN2-Pyrimidinylthio 404 CN 2-Benzothiazolylthio 405 CN Phenylthiomethyl406 CN 2-Pyridylmethyl 407 CN 3-Pyridylmethyl 408 CN Furfuryloxy 409 CNThienylmethoxy 410 CN 3-Isoxazolylmethoxy 411 CN 2-Oxazolylmethoxy 412CN 2-Pyridylmethoxy 413 CN 2′-Furyl-2-ethenyl 414 CN2′-Thienyl-2-ethenyl 415 CN 3′-Pyridyl-2-ethenyl 416 CN Oxiranyl 417 CN1-Aziridinyl 418 CN 1-Azetidinyl 419 CN 1-Pyrrolidinyl 420 CN2-Tetrahydrofuryl 421 CN 2-Tetrahydropyranyl 422 CN 3-Tetrahydropyranyl423 CN 1-Piperidinyl 424 CN 1-Morpholinyl 425 CN 1-Piperazinyl 426 CN1,3-Dioxan-2-yl 427 CN 3-Tetrahydrothiopyranyl 428 CN2-Dihydropyranyloxy 429 CN 2-Tetrahydropyranyloxy oil; IR (film): 1439,1228, 1209, 1050, 1025 767 430 CN (CH₂)₄ 431 CN (CH₂)₅ 432 CN (CH₂)₆ 433CN 434 CN 435 CN

436 CN

437 CN

438 CN

439 CN

440 CN

441 CN CF₃ 442 CN 2-Fluoroethyl 443 CN 2,2,2-Trifluoroethyl 444 CNPentafluoroethyl 445 CN Chloromethyl 446 CN Dichloromethyl 447 CNTrichloromethyl 448 CN 2-Chloroethyl 449 CN 2,2,2-Trichloroethyl 450 CNPentachloroethyl 451 CN Cyclopropyl 452 CN Cyclobutyl 453 CN Cyclopentyl454 CN Cyclohexyl 455 CN 1-Methylcyclopropyl 456 CN2,2-Dimethylcyclopropyl 457 CN 1-Methylcyclohexyl 458 CN2,2-Difluorocyclopropyl 459 CN 2,2-Dichlorocyclopropyl 460 CN2,2-Dibromocyclopropyl 461 CN 2,2-Dichloro-3-Methylcyclopropyl 462 CN2,2,3,3-Tetrafluorocyclobutyl 463 CN Ethenyl 464 CN 1-Propenyl 465 CN2-Methyl-1-propenyl 466 CN 4-Methylpent-3-en-1-yl 467 CN 2-Propenyl 468CN 2-Butenyl 469 CN 1-Methyl-2-propenyl 470 CN 3-Methyl-2-butenyl 471 CN2,2-Difluoroethenyl 472 CN 2,2-Dichloroethenyl 473 CN3,3,3-Trifluoropropenyl 474 CN 3,3,3-Trichloropropenyl 475 CN3-Chloro-2-propenyl 476 CN Cyclopent-1-enyl 477 CN Cyclopentadienyl 478CN Cyclohex-1-enyl 479 CN Pentafluorocyclopentadienyl 480 CNPentachlorocyclopentadienyl 481 CN Styryl 482 CH₃ Methoxymethyl 483 CH₃Ethoxymethyl 484 CH₃ n-Propoxymethyl 485 CH₃ iso-Propoxymethyl 486 CH₃tert.-Butoxymethyl 487 CH₃ 2-Methoxyprop-2-yl 488 CH₃ 2-Ethoxyprop-2-yl489 CH₃ 2-n-Propoxyprop-2-yl 490 CH₃ 2-iso-Propoxyprop-2-yl 491 CH₃2-tert.-Butoxyprop-2-yl 492 CH₃ Methylthiomethyl 493 CH₃tert.-Butylthiomethyl 494 CH₃ 2-Methylthioprop-2-yl 495 CH₃2-iso-Propylthioprop-2-yl 496 CH₃ 2-tert.-Butylthioprop-2-yl 497 CH₃Methyl m.p. 68-71° C.; IR (KBr): 1137, 1298, 1067, 1023, 1007, 771 498CH₃ Ethyl 499 CH₃ n-Propyl 500 CH₃ iso-Propyl 501 CH₃ n-Butyl 502 CH₃iso-Butyl 503 CH₃ sec.-Butyl 504 CH₃ tert.-Butyl 505 CH₃ n-Hexyl 506 CH₃n-Decyl 507 CH₃ Cyclopropyl 508 CH₃ Cyclohexyl 509 CH₃ Phenylthiomethyl510 CH₃ 2-Phenylthiomethyl 511 CH₃ 2-(2′-Chlorophenylthio)prop-2-yl 512CH₃ Ethynyl 513 CH₃ 1-Propynyl 514 CH₃ Methoxy 515 CH₃ Ethoxy 516 CH₃n-Propoxy 517 CH₃ iso-Propoxy 518 CH₃ n-Butoxy 519 CH₃ iso-Butoxy 520CH₃ sec.-Butoxy 521 CH₃ tert.-Butoxy 522 CH₃ Methylthio 523 CH₃Ethylthio 524 CH₃ n-Propylthio 525 CH₃ iso-Propylthio 526 CH₃n-Butylthio 527 CH₃ iso-Butylthio 528 CH₃ sec.-Butylthio 529 CH₃tert.-Butylthio 530 CH₃ Benzylthio 531 CH₃ Trifluoromethoxy 532 CH₃Cyano 533 CH₃ Amino 534 CH₃ Methylamino 535 CH₃ Dimethylamino 536 CH₃Ethylamino 537 CH₃ Diethylamino 538 CH₃ Di-n-Propylamino 539 CH₃Di-iso-Propylamino 540 CH₃ Di-n-Butylamino 541 CH₃ Di-iso-Butylamino 542CH₃ Acetyl 543 CH₃ Propion-1-yl 544 CH₃ Butyr-1-yl 545 CH₃Iso-Butyl-1-yl 546 CH₃ Pivaloyl 547 CH₃ Benzoyl 548 CH₃ 4-Chlorobenzoyl549 CH₃ Benzylcarbonyl 550 CH₃ Methoxycarbonyl 551 CH₃ Ethoxycarbonyl552 CH₃ n-Propoxycarbonyl 553 CH₃ iso-Propoxycarbonyl 554 CH₃n-Butoxycarbonyl 555 CH₃ iso-Butoxycarbonyl 556 CH₃ sec.-Butoxycarbonyl557 CH₃ tert.-Butoxycarbonyl 558 CH₃ n-Hexoxycarbonyl 559 CH₃Phenoxycarbonyl 560 CH₃ 4-Chlorophenoxycarbonyl 561 CH₃Benzyloxycarbonyl 562 CH₃ Aminocarbonyl 563 CH₃ Dimethylaminocarbonyl564 CH₃ Diethylaminocarbonyl 565 CH₃ Di-iso-Propylaminocarbonyl 566 CH₃Phenylaminocarbonyl 567 CH₃ N-Methyl-N-Phenylaminocarbonyl 568 CH₃Phenyl 569 CH₃ 2-Fluorophenyl m.p.: 89-91° C.; IR (KBr): 1732, 1071,1012, 998, 768 570 CH₃ 3-Fluorophenyl m.p.: 83-85° C.; IR (KBr): 1724,1204, 1067, 1031, 1015, 955 571 CH₃ 4-Fluorophenyl m.p.: 76-8° C.; IR(KBr): 1737, 1510, 1302, 1224, 1072, 1031, 1015, 933 572 CH₃Pentafluorophenyl 573 CH₃ 2-Chlorophenyl 574 CH₃ 3-Chlorophenyl m.p.:61-63° C.; IR (KBr): 1735, 1070, 1015, 1002, 785 575 CH₃ 4-Chlorophenyloil; IR (film): 1708, 1634, 1256, 1129 576 CH₃ Pentachlorophenyl 577 CH₃2,3-Dichlorophenyl 578 CH₃ 2,4-Dichlorophenyl 579 CH₃ 2,5-Dichlorophenyl580 CH₃ 2,6-Dichlorophenyl 581 CH₃ 3,4-Dichlorophenyl 582 CH₃3,5-Dichlorophenyl m.p.: 95-7° C.; IR (KBr): 1723, 1556, 1224, 1067,1030, 1014, 957 583 CH₃ 2,3,4-Trichlorophenyl m.p.: 118-20° C. 584 CH₃2,3,5-Trichlorophenyl 585 CH₃ 2,3,6-Trichlorophenyl 586 CH₃2,4,5-Trichlorophenyl 587 CH₃ 2,4,6-Trichlorophenyl 588 CH₃3,4,5-TrichIoroohenyl 589 CH₃ 2,3,4,6-Tetrachlorophenyl 590 CH₃2,3,5-6-Tetrachlorophenyl 591 CH₃ 2-Bromophenyl 592 CH₃ 3-Bromophenylm.p.: 80-4° C.; IR (KBr): 1723, 1556, 1224, 1067, 1030, 1014, 957 593CH₃ 4-Bromophenyl m.p.: 73-75° C.; IR (KBr): 1736, 1071, 1029, 1015, 932594 CH₃ 2,4-Dibromophenyl 595 CH₃ 3-Bromo-4-fluorophenyl 596 CH₃3-Bromo-4-methoxyphenyl 597 CH₃ 2-Iodophenyl 598 CH₃ 3-lodophenyl 599CH₃ 4-Iodophenyl 600 CH₃ 2-Chloro-4-fluorophenyl 601 CH₃2-Chloro-5-fluorophenyl 602 CH₃ 2-Chloro-6-fluorophenyl 603 CH₃2-Chloro-4-bromophenyl 604 CH₃ 2-Bromo-4-chlorophenyl 605 CH₃2-Bromo-4-fluorophenyl 606 CH₃ 3-Bromo-4-chlorophenyl 607 CH₃3-Chloro-4-fluorophenyl 608 CH₃ 3-Fluoro-4-chlorophenyl 609 CH₃2-Cyanophenyl 610 CH₃ 3-Cyanophenyl 611 CH₃ 4-Cyanophenyl 612 CH₃2-Nitrophenyl 613 CH₃ 3-Nitrophenyl 614 CH₃ 4-Nitrophenyl m.p.: 88-90°C.; IR (KBr): 1725, 1512, 1342, 1219, 1068, 1009, 854 615 CH₃2-Methylphenyl 616 CH₃ 3-Methylphenyl m.p.: 93-96° C. 617 CH₃4-Methylphenyl m.p.: 82-84° C.; IR (KBr): 1722, 1068, 1038, 1015, 920618 CH₃ 2,4-Dimethylphenyl 619 CH₃ 2,6-Dimethylphenyl 620 CH₃3,4-Dimethylphenyl 621 CH₃ 3,5-Dimethylphenyl 622 CH₃2,3,4-Trimethylphenyl 623 CH₃ 2,3,5-Trimethylphenyl 624 CH₃2,3,6-Trimethylphenyl 625 CH₃ 2,4,5-Trimethylphenyl 626 CH₃2,4,6-Trimethylphenyl 627 CH₃ 3,4,5-Trimethylphenyl 628 CH₃Pentamethylphenyl 629 CH₃ 2-Ethylphenyl 630 CH₃ 3-Ethylphenyl 631 CH₃4-Ethylphenyl 632 CH₃ 3,5-Diethylphenyl 633 CH₃ 2-n-Propylphenyl 634 CH₃3-n-Propylphenyl 635 CH₃ 4-n-Propylphenyl 636 CH₃ 2-iso-Propylphenyl 637CH₃ 3-iso-Propylphenyl 638 CH₃ 4-iso-Propylphenyl 639 CH₃2,4-Di-iso-Propylphenyl 640 CH₃ 3,5-Di-iso-Propylphenyl 641 CH₃4-n-Butylphenyl 642 CH₃ 4-sec.-Butylphenyl 643 CH₃ 4-iso-Butylphenyl 644CH₃ 4-tert.-Butylphenyl m.p.: 45-50° C. 645 CH₃ 3-tert.-Butylphenyl 646CH₃ 2-tert.-Butylphenyl 647 CH₃ 2,4-Di-tert.-Butylphenyl 648 CH₃3,5-Di-tert.-Butylphenyl 649 CH₃ 4-n-Hexylphenyl 650 CH₃4-n-Dodecylphenyl 651 CH₃ 2-Methyl-4-tert.-Butylphenyl 652 CH₃2-Methyl-6-tert.-Butylphenyl 653 CH₃ 2-Methyl-4-iso-Propylphenyl 654 CH₃2-Methyl-4-Cyclohexylphenyl 655 CH₃ 2-Methyl-4-Phenylphenyl 656 CH₃2-Methyl-4-Benzylphenyl 657 CH₃ 2-Methyl-4-Phenoxyphenyl 658 CH₃2-Methyl-4-Benzyloxyphenyl 659 CH₃ 2-Methyl-3-Chlorophenyl 660 CH₃2-Methyl-4-Chlorophenyl 661 CH₃ 2-Methyl-5-Chlorophenyl 662 CH₃2-Methyl-6-chlorophenyl 663 CH₃ 2-Methyl-4-fluorophenyl 664 CH₃2-Methyl-3-bromophenyl 665 CH₃ 2-Methyl-4-bromophenyl 666 CH₃2-Methyl-3-methoxyphenyl 667 CH₃ 2-Methyl-4-methoxyphenyl 668 CH₃2-Methyl-5-methoxyphenyl 669 CH₃ 2-Methyl-6-methoxyphenyl 670 CH₃2-Methyl-4-iso-Propoxyphenyl 671 CH₃ 2-Methyl-2,5-dimethoxyphenyl 672CH₃ 2-Methoxyphenyl m.p.: 74-6° C.; IR (KBr): 1741, 1433, 1295, 1249,1224, 1067, 1022, 878 673 CH₃ 3-Methoxyphenyl 674 CH₃ 4-Methoxyphenylm.p.: 90-91° C. 675 CH₃ 2,3-Dimethoxyphenyl 676 CH₃ 2,4-Dimethoxyphenyl677 CH₃ 2,5-Dimethoxyphenyl 678 CH₃ 2,6-Dimethoxyphenyl 679 CH₃3,4-Dimethoxyphenyl 680 CH₃ 3,5-Dimethoxyphenyl 681 CH₃3,6-Dimethoxyphenyl 682 CH₃ 2,3,4-Trimethoxyphenyl 683 CH₃2,3,5-Trimethoxyphenyl 684 CH₃ 2,3,5-Trimethoxyphenyl 685 CH₃2,4,5-Trimethoxyphenyl 686 CH₃ 2,4,6-Trimethoxyphenyl 687 CH₃3,4,5-Trimethoxyphenyl 688 CH₃ 2-Ethoxyphenyl 689 CH₃ 3-Ethoxyphenyl 690CH₃ 4-Ethoxyphenyl 691 CH₃ 2-iso-Propoxyphenyl 692 CH₃3-iso-Propoxyphenyl 693 CH₃ 4-iso-Propoxyphenyl 694 CH₃3-tert.-Butoxyphenyl 695 CH₃ 4-tert.-Butoxyphenyl 696 CH₃2-Trifluoromethoxyphenyl 697 CH₃ 3-Trifluoromethoxyphenyl 698 CH₃4-Trifluoromethoxyphenyl 699 CH₃ 3-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl700 CH₃ 4-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl 701 CH₃2-Chloromethylphenyl 702 CH₃ 3-Chloromethylphenyl 703 CH₃4-Chloromethylphenyl 704 CH₃ 2-Trifluoromethylphenyl m.p.: 78-80° C.; IR(KBr): 1741, 1315, 1116, 1068, 1010 705 CH₃ 3-Trifluoromethylphenylm.p.: 70-72° C.; IR (KBr): 1740, 1297, 1281, 1164, 1124, 1073, 1010 706CH₃ 4-Trifluoromethylphenyl m.p.: 57-58° C.; (IR (KBr): 1728, 1333,1318, 1106, 1069, 986 707 CH₃ 2-(Methoxyiminomethyl)phenyl 708 CH₃3-(Methoxyiminomethyl)phenyl 709 CH₃ 4-(Methoxyiminomethyl)phenyl 710CH₃ 2-(Ethoxyiminomethyl)phenyl 711 CH₃ 3-(Ethoxyiminomethyl)phenyl 712CH₃ 4-(Ethoxyiminomethyl)phenyl 713 CH₃ 2-(n-Propoxyiminomethyl)phenyl714 CH₃ 3-(n-Propoxyiminomethyl)phenyl 715 CH₃4-(n-Propoxyiminomethyl)phenyl 716 CH₃ 2-(iso-Propoxyiminomethyl)phenyl717 CH₃ 3-(iso-Propoxyiminomethyl)phenyl 718 CH₃4-(iso-Propoxyiminomethyl)phenyl 719 CH₃ 2-(n-Butoxyiminomethyl)phenyl720 CH₃ 3-(n-Butoxyiminomethyl)phenyl 721 CH₃4-(n-Butoxyiminomethyl)phenyl 722 CH₃ 2-(iso-Butoxyiminomethyl)phenyl723 CH₃ 3-(iso-Butoxyiminomethyl)phenyl 724 CH₃4-(iso-Butoxyiminomethyl)phenyl 725 CH₃2-(tert.-Butoxyiminomethyl)phenyl 726 CH₃3-(tert.-Butoxyiminomethyl)phenyl 727 CH₃4-(tert.-Butoxyiminomethyl)phenyl 728 CH₃ 2-(n-Pentoxyiminomethyl)phenyl729 CH₃ 3-(n-Pentoxyimonomethyl)phenyl 730 CH₃4-(n-Pentoxyiminomethyl)phenyl 731 CH₃ 2-(n-Hexoxyiminomethyl)phenyl 732CH₃ 3-(n-Hexoxyiminomethyl)phenyl 733 CH₃ 4-(n-Hexoxyiminomethyl)phenyl734 CH₃ 2-(Allyloxyiminomethyl)phenyl 735 CH₃3-(Allyloxyiminomethyl)phenyl 736 CH₃ 4-(Allyloxyiminomethyl)phenyl 737CH₃ 2-(Benzyloxyiminomethyl)phenyl 738 CH₃3-(Benzyloxyiminomethyl)phenyl 739 CH₃ 4-(Benzyloxyiminomethyl)phenyl740 CH₃ 2-(Methoxyimlno-1′-ethyl)phenyl 741 CH₃3-(Methoxyimino-1′-ethyl)phenyl 742 CH₃ 4-(Methcxyimino-1′-ethyl)phenyl743 CH₃ 2-(Ethoxyimino-1′-ethyl)phenyl 744 CH₃3-(Ethoxyimino-1′-ethyl)phenyl 745 CH₃ 4-(Ethoxyimino-1′-ethyl)phenyl746 CH₃ 2-(n-Propoxyimino-1′-ethyl)phenyl 747 CH₃3-(n-Propoxyimino-1′-ethyl)phenyl 748 CH₃4-(n-Propoxyimino-1′-ethyl)phenyl 749 CH₃2-(n-Butoxyamino-1′-ethyl)phenyl 750 CH₃3-(n-Butoxyamino-1′-ethyl)phenyl 751 CH₃4-(n-Butoxyamino-1′-ethyl)phenyl 752 CH₃2-(n-Pentoxyimino-1′-ethyl)phenyl 753 CH₃3-(n-Pentoxyimino-1′-ethyl)phenyl 754 CH₃4-(n-Pentoxyimino-1′-ethyl)phenyl 755 CH₃2-(n-Hexoxyimino-1′-ethyl)phenyl 756 CH₃3-(n-Hexoxyomino-1′-ethyl)phenyl 757 CH₃4-(n-Hexoxyimino-1′-ethyl)phenyl 758 CH₃2-(Allyloxyimino-1′-ethyl)phenyl 759 CH₃3-(Allyloxyimino-1′-ethyl)phenyl 760 CH₃4-(Allyloxyimino-1′-ethyl)phenyl 761 CH₃2-(Benzyloxyimino-1′-ethyl)phenyl 762 CH₃3-(Benzyloxyimino-1′-ethyl)phenyl 763 CH₃4-(Benzyloxyimino-1′-ethyl)phenyl 764 CH₃ 2-Phenylphenyl 765 CH₃3-Phenylphenyl 766 CH₃ 4-Phenylphenyl 767 CH₃ 2-Phenoxyphenyl 768 CH₃3-Phenoxyphenyl 769 CH₃ 4-Phenoxyphenyl m.p.: 91-3° C.; IR (KBr): 1732,1587, 1491, 1241, 1071, 1014, 995, 769 770 CH₃ 2-Benzyloxyphenyl 771 CH₃3-Benzyloxyphenyl 772 CH₃ 4-Benzyloxyphenyl 773 CH₃4-(Imidazol-1′-yl)phenyl 774 CH₃ 4-(Piperazin-1′-yl)phenyl 775 CH₃4-(Morpholin-1′-yl)phenyl 776 CH₃ 4-(Piperidin-1′-yl)phenyl 777 CH₃4-(Pyridyl-2′-oxy)phenyl 778 CH₃ 2-Cyclopropylphenyl 779 CH₃3-Cyclopropylphenyl 780 CH₃ 4-Cyclopropylphenyl 781 CH₃3-Cyclohexylphenyl 782 CH₃ 4-Cyclohexylphenyl m.p.: 53-5° C. 783 CH₃4-Oxiranylphenyl 784 CH₃ 4-(1′,3′-Dioxan-2′-yl)phenyl 785 CH₃4-(Tetrahydropyran-2-yloxy)phenyl 786 CH₃ 1-Naphthyl 787 CH₃ 2-Naphthyl788 CH₃ 9-Anthryl 789 CH₃ 1-Naphthoxy 790 CH₃ 2-Naphthoxy 791 CH₃9-Anthroxy 792 CH₃ Phenoxy 793 CH₃ 2-Chlorophenoxy 794 CH₃3-Chlorophenoxy 795 CH₃ 4-Chlorophenoxy 796 CH₃ 4-Methylphenoxy 797 CH₃4-tert.-Butylphenoxy 798 CH₃ 4-Methoxyphenoxy 799 CH₃ 4-Ethoxyphenoxy800 CH₃ 4-tert.-Butoxyphenoxy 801 CH₃ Phenylthio 802 CH₃2-Chlorophenylthio 803 CH₃ 4-Chlorophenylthio 894 CH₃ Benzyl 805 CH₃2-Methylbenzyl 806 CH₃ 3-Methylbenzyl 807 CH₃ 4-Methylbenzyl 808 CH₃4-tert.-Butylbenzyl 809 CH₃ 2-Chlorobenzyl 810 CH₃ 3-Chlorobenzyl 811CH₃ 4-Chlorobenzyl 812 CH₃ 2,4-Dichlorobenzyl 813 CH₃ 2,6-Dichlorobenzyl814 CH₃ 2,4,6-Trichlorobenzyl 815 CH₃ 2-Trifluoromethylbenzyl 816 CH₃3-Trifluoromethylbenzyl 817 CH₃ 4-Trifluoromethylbenzyl 818 CH₃2-Methoxybenzyl 819 CH₃ 4-Methoxybenzyl 820 CH₃ 4-tert.-Butoxybenzyl 821CH₃ 4-Phenoxybenzyl 822 CH₃ 1-Phenethyl 823 CH₃ 2-Phenethyl 824 CH₃1-Phenylpropyl 825 CH₃ 2-Phenylpropyl 826 CH₃ 3-Phenylpropyl 827 CH₃2-Methyl-2-phenylpropyl 828 CH₃ 2-Methyl-3-phenylpropyl 829 CH₃4-Phenylbutyl 830 CH₃ 2-Phenyl-1-ethenyl 831 CH₃ 1-Phenyl-1-ethenyl 832CH₃ 1-Phenyl-1-propenyl 833 CH₃ 1-Phenyl-1-propen-2-yl 834 CH₃2,2-Diphenylethenyl 835 CH₃ Phenoxymethyl 836 CH₃ 2-Pyridyl 837 CH₃3-Pyridyl 838 CH₃ 4-Pyridyl 839 CH₃ 2,6-Pyrimidinyl 840 CH₃1,5-Pyrimidinyl 841 CH₃ 2-Thienyl 842 CH₃ 3-Thienyl 843 CH₃ 2-Furyl 844CH₃ 3-Furyl 845 CH₃ 1-Pyrrolyl 846 CH₃ 1-Imidazolyl 847 CH₃1,2,4-Triazolyl 848 CH₃ 1,3,4-Triazolyl 849 CH₃ 4-Thiazolyl 850 CH₃2-Benzothiazolyl 851 CH₃ 2-Pyridyloxy 852 CH₃ 2-Pyrimidinyloxy 853 CH₃2-Pyridylthio 854 CH₃ 2-Pyrimidinylthio 855 CH₃ 2-Benzothiazolylthio 856CH₃ Phenylthiomethyl 857 CH₃ 2-Pyridylmethyl 858 CH₃ 3-Pyridylmethyl 859CH₃ Furfuryloxy 860 CH₃ Thienylmethoxy 861 CH₃ 3-Isoxazolylmethoxy 862CH₃ 2-Oxazolylmethoxy 863 CH₃ 2-Pyridylmethoxy 864 CH₃2′-Furyl-2-ethenyl 865 CH₃ 2′-Thienyl-2-ethenyl 866 CH₃3′-Pyridyl-2-ethenyl 867 CH₃ Oxiranyl 868 CH₃ 1-Aziridinyl 869 CH₃1-Azetidinyl 870 CH₃ 1-Pyrrolidinyl 871 CH₃ 2-Tetrahydrofuryl 872 CH₃2-Tetrahydropyranyl 873 CH₃ 3-Tetrahydropyranyl 874 CH₃ 1-Piperidinyl875 CH₃ 1-Morpholinyl 876 CH₃ 1-Piperazinyl 877 CH₃ 1,3-Dioxan-2-yl 878CH₃ 3-Tetrahydrothiopyranyl 879 CH₃ 2-Dihydropyranyloxy 880 CH₃2-Tetrahydropyranyloxy 881 CH₃ CF₃ 882 CH₃ 2-Fluoroethyl 883 CH₃2,2,2-Trifluoroethyl 884 CH₃ Pentafluoroethyl 885 CH₃ Chloromethyl 886CH₃ Dichloromethyl 887 CH₃ Trichloromethyl 888 CH₃ 2-Chloroethyl 889 CH₃2,2,2-Trichloroethyl 890 CH₃ Pentachloroethyl 891 CH₃ Cyclopropyl 892CH₃ Cyclobutyl 893 CH₃ Cyclopentyl 894 CH₃ Cyclohexyl 895 CH₃1-Methylcyclopropyl 896 CH₃ 2,2-Dimethylcyclopropyl 897 CH₃1-Methylcyclohexyl 898 CH₃ 2,2-Difluorocyclopropyl 899 CH₃2,2-Dichlorocyclopropyl 900 CH₃ 2,2-Dibromocyclopropyl 901 CH₃2,2-Dichloro-3-Methylcyclopropyl 902 CH₃ 2,2,3,3-Tetrafluorocyclobutyl903 CH₃ Ethenyl 904 CH₃ 1-Propenyl 905 CH₃ 2-Methyl-1-propenyl 906 CH₃4-Methylpent-3-en-1-yl 907 CH₃ 2-Propenyl 908 CH₃ 2-Butenyl 909 CH₃1-Methyl-2-propenyl 910 CH₃ 3-Methyl-2-butenyl 911 CH₃2,2-Difluoroethenyl 912 CH₃ 2,2-Dichloroethenyl 913 CH₃3,3,3-Trifluoropropenyl 914 CH₃ 3,3,3-Trichloropropenyl 915 CH₃3-Chloro-2-propenyl 916 CH₃ Cyclopent-1-enyl 917 CH₃ Cyclopentadienyl918 CH₃ Cyclohex-1-enyl 919 CH₃ Pentafluorocyclopentadienyl 920 CH₃Pentachlorocyclopentadienyl 921 Phenyl Phenyl 922 Phenyl 2-Fluorophenyl923 Phenyl 4-Fluorophenyl 924 Phenyl 2-Chlorophenyl 925 Phenyl3-Chlorophenyl 926 Phenyl 4-Chlorophenyl 927 Phenyl 3,4-Dichlorophenyl928 Phenyl 4-Nitrophenyl 929 Phenyl 2-CF₃-Phenyl 930 Phenyl 3-CF₃-Phenyl931 Phenyl 4-CF₃-Phenyl 932 Phenyl 2-Methylphenyl 933 Phenyl3-Methylphenyl 934 Phenyl 4-Methylphenyl 935 Phenyl 2,4-Dimethylphenyl936 Phenyl 4-tert.-Butylphenyl 937 Phenyl 4-Methoxyphenyl 9384-Fluorophenyl 4-Fluorophenyl 939 2-Fluorophenyl 4-Fluorophenyl 9402-Chlorophenyl 4-Fluorophenyl 941 2-Chlorophenyl 2-Chlorophenyl 9423-Chlorophenyl 3-Chlorophenyl 943 4-Chlorophenyl 4-Chlorophenyl 9442-Chlorophenyl 4-Chlorophenyl 945 4-Methoxyphenyl 4-Methoxyphenyl 9464-Dimethyl- 4-Dimethylaminophenyl aminophenyl 947 Phenyl Naphthyl 948Ethyl Ethyl 949 Ethyl n-Propyl 950 Ethyl iso-Propyl 951 Ethyl n-Butyl952 Ethyl iso-Butyl 953 Ethyl 2-Methyl-butyl 954 Ethyl Benzyl 955n-Propyl n-Propyl 956 iso-Propyl iso-Propyl 957 n-Butyl n-Butyl 958iso-Butyl iso-Butyl 959 tert.-Butyl tert.-Butyl 960 Benzyl Benzyl 961Pentachloroethyl Pentachloroethyl 962 n-Hexyl n-Hexyl 963 EthoxycarbonylEthoxycarbonyl 964 Phenyl Benzoyl 965 Ethyl Phenyl 966 n-Butyl Phenyl967 Styryl Styryl 968 2-Pyridyl 2-Pyridyl 969 3-Pyridyl 3-Pyridyl 970Ethyl 2-Pyridyl m.p.: 84-86° C. 971

m.p.: 103-105° C.

TABLE III

No. X Y R¹ R²═H R³ R⁴ Data 1 CHS—CH₃ O CH₃ CF₃ Phenyl 2 CHS—CH₃ O CH₃Cyclopropyl Phenyl 3 CHS—CH₃ O CH₃ Cyclopropyl 4-Chlorophenyl 4 CHS—CH₃O CH₃ Cyclopropyl 4-Methoxyphenyl 5 CHS—CH₃ O CH₃ Cyclopropyl4-tert.-Butylphenyl 6 CHS—CH₃ O CH₃ CN Methylthio 7 CHS—CH₃ O CH₃ CN2-Methoxyprop-2-yl 8 CHS—CH₃ O CH₃ CN 2-Methylthioprop-2-yl 9 CHS—CH₃ OCH₃ CN Phenylthio 10 CHS—CH₃ O CH₃ CN iso-Propyl 11 CHS—CH₃ O CH₃ CN CN12 CHS—CH₃ O CH₃ CN Acetyl 13 CHS—CH₃ O CH₃ CN Benzoyl 14 CHS—CH₃ O CH₃CN Methoxycarbonyl 15 CHS—CH₃ O CH₃ CN Phenyl No. X Y R¹ R³ R⁴ Data 16CHS—CH₃ O CH₃ CN 2-Chlorophenyl 17 CHS—CH₃ O CH₃ CN 4-Chlorophenyl 18CHS—CH₃ O CH₃ CN 2-Methylphenyl 19 CHS—CH₃ O CH₃ CN 4-tert.-Butylphenyl20 CHS—CH₃ O CH₃ CN 4-(n-Butoxyiminomethyl)phenyl 21 CHS—CH₃ O CH₃ CN2-Pyridyl 22 CHS—CH₃ O CH₃ CN styryl 23 CHS—CH₃ O CH₃ CN 1-Propenyl 24CHS—CH₃ O CH₃ CH₃ Phenylthio 25 CHS—CH₃ O CH₃ CH₃ Benzyl 26 CHS—CH₃ OCH₃ CH₃ tert.-Butyl 27 CHS—CH₃ O CH₃ CH₃ iso-Propyl 28 CHS—CH₃ O CH₃ CH₃2-Methylbutyl 29 CHS—CH₃ O CH₃ CH₃ iso-Butyl 30 CHS—CH₃ O CH₃ CH₃ Phenyl31 CHS—CH₃ O CH₃ CH₃ 2-Chlorophenyl 32 CHS—CH₃ O CH₃ CH₃ 4-Chlorophenyl33 CHS—CH₃ O CH₃ CH₃ 2-Methylphenyl 34 CHS—CH₃ O CH₃ CH₃ Naphthyl 35CHS—CH₃ O CH₃ CH₃ 1-Pyridyl 36 CHS—CH₃ O CH₃ iso-Butyl Iso-Butyl 37CHS—CH₃ O CH₃ Phenyl Phenyl 38 CHS—CH₃ O CH₃ CH₂CH₂CH₂CH₂ 39 CHS—CH₃ OCH₃ CH₂CH₂CH₂CH₂CH₂ 40 CH—CH₃ O CH₃ CF₃ Phenyl 41 CH—CH₃ O CH₃Cyclopropyl Phenyl 42 CH—CH₃ O CH₃ Cyclopropyi 4-Chlorophenyl 43 CH—CH₃O CH₃ Cyclopropyl 4-Methoxyphenyl 44 CH—CH₃ O CH₃ Cyclopropyl4-tert.-Butylphenyl 45 CH—CH₃ O CH₃ CN Methylthio 46 CH—CH₃ O CH₃ CN2-Methoxyprop-2-yl IR(film): 1717, 1436, 1367, 1256, 1210, 1179, 1070,1037, 1009, 759 47 CH—CH₃ O CH₃ CN 2-Methylthioprop-2-yl ¹H-NMR(CDCl₃):δ=1.45s, 1.6d, 1.8s, 3.7s, 5.1s, 7.1-7.5m 48 CH—CH₃ O CH₃ CN Phenylthio49 CH—CH₃ O CH₃ CN iso-Propyl ¹H-NMR(CDCl₃): δ=1.2d, 1.6d, 2.7m, 3.67s,5.1s, 7.0-7.5m 50 CH—CH₃ O CH₃ CN CN 51 CH—CH₃ O CH₃ CN Acetyl 52 CH—CH₃O CH₃ CN Benzoyl 53 CH—CH₃ O CH₃ CN Methoxycarbonyl 54 CH—CH₃ O CH₃ CNPhenyl ¹H-NMR(CDCl₃):δ=1.6d, 3.7s, 5.2s, 7.0-1.8m 55 CH—CH₃ O CH₃ CN2-Chlorophenyl 56 CH—CH₃ O CH₃ CN 4-Chlorophenyl 57 CH—CH₃ O CH₃ CN2-Methylphenyl 58 CH—CH₃ O CH₃ CN 4-tert.-Butylphenyl 59 CH—CH₃ O CH₃ CN4-(n-Butoxyiminomethyl)phenyl 60 CH—CH₃ O CH₃ CN 2-Pyridyl 61 CH—CH₃ OCH₃ CN Styryl 62 CH—CH₃ O CH₃ CN 1-Propenyl 63 CH—CH₃ O CH₃ CH₃Phenylthio 64 CH—CH₃ O CH₃ CH₃ Benzyl 65 CH—CH₃ O CH₃ CH₃ tert.-Butyl 66CH—CH₃ O CH₃ CH₃ iso-Propyl 67 CH—CH₃ O CH₃ CH₃ 2-Methylbutyl 68 CH—CH₃O CH₃ CH₃ iso-Butyl 69 CH—CH₃ O CH₃ CH₃ Phenyl 70 CH—CH₃ O CH₃ CH₃2-Chlorophenyl 71 CH—CH₃ O CH₃ CH₃ 4-Chlorophenyl IR(film): 1716, 1490,1434, 1253, 1206, 1096, 1036, 1012, 820, 760 72 CH—CH₃ O CH₃ CH₃2-Methylphenyl 73 CH—CH₃ O CH₃ CH₃ Naphthyl 74 CH—CH₃ O CH₃ CH₃1-Pyridyl 75 CH—CH₃ O CH₃ iso-Butyl iso-Butyl 76 CH—CH₃ O CH₃ PhenylPhenyl 77 CH—CH₃ O CH₃ CH₂CH₂CH₂CH₂ 78 CH—CH₃ O CH₃ CH₂CH₂CH₂CH₂CH₂ 79CH₂ O CH₃ CF₃ Phenyl 80 CH₂ O CH₃ Cyclopropyl Phenyl 81 CH₂ O CH₃Cyclopropyl 4-Chlorophenyl 82 CH₂ O CH₃ Cyclopropyl 4-Methoxyphenyl 83CH₂ O CH₃ Cyclopropyl 4-tert.-Butylphenyl 84 CH₂ O CH₃ CN Methylthio 85CH₂ O CH₃ CN 2-Methoxyprop-2-yl 86 CH₂ O CH₃ CN 2-Methylthioprop-2-yl 87CH₂ O CH₃ CN Phenylthio 88 CH₂ O CH₃ CN iso-Propyl 89 CH₂ O CH₃ CN CN 90CH₂ O CH₃ CN Acetyl 91 CH₂ O CH₃ CN Benzoyl 92 CH₂ O CH₃ CNMethoxycarbonyl 93 CH₂ O CH₃ CN Phenyl 94 CH₂ O CH₃ CN 2-Chlorophenyl 95CH₂ O CH₃ CN 4-Chlorophenyl 96 CH₂ O CH₃ CN 2-Methylphenyl 97 CH₂ O CH₃CN 4-tert.-Butylphenyl 98 CH₂ O CH₃ CN 4-(n-Butoxylminomethyl)phenyl 99CH₂ O CH₃ CN 2-Pyridyl 100 CH₂ O CH₃ CN Styryl 101 CH₂ O CH₃ CN1-Prepenyl 102 CH₂ O CH₃ CH₃ Phenylthio 103 CH₂ O CH₃ CH₃ Benzyl 104 CH₂O CH₃ CH₃ tert.-Butyl 105 CH₂ O CH₃ CH₃ iso-Propyl 106 CH₂ O CH₃ CH₃2-Methylbutyl 107 CH₂ O CH₃ CH₃ iso-Butyl 108 CH₂ O CH₃ CH₃ Phenyl 109CH₂ O CH₃ CH₃ 2-Chlorophenyl 110 CH₂ O CH₃ CH₃ 4-Chlorophenyl 111 CH₂ OCH₃ CH₃ 2-Methylphenyl 112 CH₂ O CH₃ CH₃ Naphthyl 113 CH₂ O CH₃ CH₃1-Pyridyl 114 CH₂ O CH₃ iso-Butyl iso-Butyl 115 CH₂ O CH₃ Phenyl Phenyl116 CH₂ O CH₃ CH₂CH₂CH₂CH₂ 117 CH₂ O CH₃ CH₂CH₂CH₂CH₂CH₂ 118 N—OCH₃ SCH₃ CF₃ Phenyl 119 N—OCH₃ S CH₃ Cyclopropyl Phenyl 120 N—OCH3 S CH₃Cyclopropyl 4-Chlorophenyl 121 N—OCH₃ S CH₃ Cyclopropyl 4-Methoxyphenyl122 N—OCH₃ S CH₃ Cyclopropyl 4-tert.-Butylphenyl 123 N—OCH₃ S CH₃ CNMethylthio 124 N—OCH₃ S CH₃ CN 2-Methoxyprop-2-yl 125 N—OCH₃ S CH₃ CN2-Methylthioprop-2-yl 126 N—OCH₃ S CH₃ CN Phenylthio 127 N—OCH₃ S CH₃ CNiso-Propyl 128 N—OCH₃ S CH₃ CN CN 129 N—OCH₃ S CH₃ CN Acetyl 130 N—OCH₃S CH₃ CN Benzoyl 131 N—OCH₃ S CH₃ CN Methoxycarbonyl 132 N—OCH₃ S CH₃ CNPhenyl 133 N—OCH₃ S CH₃ CN 2-Chlorophenyl 134 N—OCH₃ S CH₃ CN4-Chlorophenyl 135 N—OCH₃ S CH₃ CN 2-Methylphenyl 136 N—OCH₃ S CH₃ CN4-tert.-Butylphenyl 137 N—OCH₃ S CH₃ CN 4-(n-Butoxylminomethyl)phenyl138 N—OCH₃ S CH₃ CN 2-Pyridyl 139 N—OCH₃ S CH₃ CN Styryl 140 N—OCH3 SCH₃ CN 1-Propenyl 141 N—OCH₃ S CH₃ CH₃ Phenylthio 142 N—OCH₃ S CH₃ CH₃Benzyl 143 N—OCH₃ S CH₃ CH₃ tert.-Butyl 144 N—OCH₃ S CH₃ CH₃ iso-Propyl145 N—OCH₃ S CH₃ CH₃ 2-Methylbutyl 146 N—OCH₃ S CH₃ CH₃ iso-Butyl 147N—OCH₃ S CH₃ CH₃ Phenyl 148 N—OCH₃ S CH₃ CH₃ 2-Chlorophenyl 149 N—OCH₃ SCH₃ CH₃ 4-Chlorophenyl 150 N—OCH₃ S CH₃ CH₃ 2-Methylphenyl 151 N—OCH₃ SCH₃ CH₃ Naphthyl 152 N—OCH₃ S CH₃ CH₃ 1-Pyridyl 153 N—OCH₃ S CH₃iso-Butyl iso-Butyl 154 N—OCH₃ S CH₃ Phenyl Phenyl 155 N—OCH₃ S CH₃CH₂CH₂CH₂CH₂ 156 N—OCH₃ S CH₃ CH₂CH₂CH₂CH₂CH₂ 157 N—OCH₃ NH CH₃ CF₃Phenyl 158 N—OCH₃ NH CH₃ Cyclopropyl Phenyl 159 N—OCH₃ NH CH₃Cyclopropyl 4-Chlorophenyl m.p.: 71-74° C. IR(KBr): 3348, 1663, 1529,1042, 1030, 982 160 N—OCH₃ NH CH₃ Cyclopropyl 4-Methoxyphenyl 161 N—OCH₃NH CH₃ Cyclopropyl 4-tert.-Butylphenyl 162 N—OCH₃ NH CH₃ CN Methylthio163 N—OCH₃ NH CH₃ CN 2-Methoxyprop-2-yl 164 N—OCH₃ NH CH₃ CN2-Methylthioprop-2-yl 165 N—OCH₃ NH CH₃ CN Phenylthio 166 N—OCH₃ NH CH₃CN iso-Propyl 167 N—OCH₃ NH CH₃ CN CN 168 N—OCH₃ NH CH₃ CN Acetyl 169N—OCH₃ NH CH₃ CN Benzoyl 170 N—OCH₃ NH CH₃ CN Methoxycarbonyl 171 N—OCH₃NH CH₃ CN Phenyl 172 N—OCH₃ NH CH₃ CN 2-Chlorophenyl 173 N—OCH₃ NH CH₃CN 4-Chlorophenyl 174 N—OCH₃ NH CH₃ CN 2-Methylphenyl 175 N—OCH₃ NH CH₃CN 4-tert.-Butylphenyl 176 N—OCH₃ NH CH₃ CN4-(n-Butoxyiminomethyl)phenyl 177 N—OCH₃ NH CH₃ CN 2-Pyridyl 178 N—OCH₃NH CH₃ CN Styryl 179 N—OCH₃ NH CH₃ CN 1-Propenyl 180 N—OCH₃ NH CH₃ CH₃Phenylthio 181 N—OCH₃ NH CH₃ CH₃ Benzyl 182 N—OCH₃ NH CH₃ CH₃tert.-Butyl 183 N—OCH₃ NH CH₃ CH₃ iso-Propyl 184 N—OCH₃ NH CH₃ CH₃2-Methylbutyl 185 N—OCH₃ NH CH₃ CH₃ iso-Butyl 186 N—OCH₃ NH CH₃ CH₃Phenyl 187 N—OCH₃ NH CH₃ CH₃ 2-Chlorophenyl 188 N—OCH₃ NH CH₃ CH₃4-Chlorophenyl m.p.: 119-121° C. IR(KBr): 3421, 1676, 1037, 985, 933,752 189 N—OCH₃ NH CH₃ CH₃ 2-Methylphenyl No. X Y R¹ R² R³ R⁴ Data 190N-OCH₃ NH CH₃ H CH₃ Naphthyl 191 N-OCH₃ NH CH₃ H CH₃ 1-Pyridyl 192N-OCH₃ NH CH₃ H iso-Butyl iso-Butyl 193 N-OCH₃ NH CH₃ H Phenyl Phenyl194 N-OCH₃ NH CH₃ H CH₂CH₂CH₂CH₂ 195 N-OCH₃ NH CH₃ H CH₂CH₂CH₂CH₂CH₂ 196N-OCH₃ O C₂H₅ H CH₃ Phenyl 197 CH-OCH₃ O C₂H₅ H CH₃ Phenyl 198 N-OCH₃ On-C₃H₅ H CH₃ Phenyl 199 CHOCH₃ O n-C₃H₅ H CH₃ Phenyl 200 CHC₂H₅ O CH₃ HCH₃ Phenyl 201 N-OCH₃ O CH₃ CH₃ CH₃ Phenyl 202 CHOCH₃ O CH₃ CH₃ CH₃Phenyl 203 N-OCH₃ O CH₃ CH₃ CN Phenyl 204 CHOCH₃ O CH₃ CH₃ CN Phenyl 205CHS—CH₃ O CH₃ H H Phenyl 206 CH—CH₃ O CH₃ H H Phenyl 207 CH₂ O CH₃ H HPhenyl 208 NOCH₃ S CH₃ H H Phenyl 209 CHOCH₃ S CH₃ H H Phenyl 210 CHOCH₃NH CH₃ H H Phenyl 211 NOCH₃ NH CH₃ H H Phenyl 212 CH—OCH₃ S CH₃ H CNMethylthio No. X Y R¹ R²═H R³ R⁴ Data 213 CH—OCH₃ S CH₃ CN2-Methoxyprop-2-yl 214 CH—OCH₃ S CH₃ CN 2-Methylthioprop-2-yl 215CH—OCH₃ S CH₃ CN Phenylthio 216 CH—OCH₃ S CH₃ CN iso-Propyl 217 CH—OCH₃S CH₃ CN CN 218 CH—OCH₃ S CH₃ CN Acthyl 219 CH—OCH₃ S CH₃ CN Benzoyl 220CH—OCH₃ S CH₃ CN Methoxycarbonyl 221 CH—OCH₃ S CH₃ CN Phenyl 222 CH—OCH₃S CH₃ CN 2-Chlorophenyl 223 CH—OCH₃ S CH₃ CN 4-Chlorophenyl 224 CH—OCH₃S CH₃ CN 2-Methylphenyl 225 CH—OCH₃ S CH₃ CN 4-tert.-Butylphenyl 226CH—OCH₃ S CH₃ CN 4-(n-Butoxyiminomethyl) 227 CH—OCH₃ S CH₃ CN 2-Pyridyl228 CH—OCH₃ S CH₃ CN Styryl 229 CH—OCH₃ S CH₃ CN 1-Propenyl 230 CH—OCH₃NH CH₃ CN Methylthio 231 CH—OCH₃ NH CH₃ CN 2-Methoxyprop-2-yl 232CH—OCH₃ NH CH₃ CN 2-Methylthioprop-2-yl 233 CH—OCH₃ NH CH₃ CN Phenylthio234 CH—OCH₃ NH CH₃ CN iso-Propyl 235 CH—OCH₃ NH CH₃ CN CN 236 CH—OCH₃ NHCH₃ CN acetyl 237 CH—OCH₃ NH CH₃ CN Benzoyl 238 CH—OCH₃ NH CH₃ CNMethoxycarbonyl 239 CH—OCH₃ NH CH₃ CN Phenyl 240 CH—OCH₃ NH CH₃ CN2-Chlorophenyl 241 CH—OCH₃ NH CH₃ CN 4-Chlorophenyl 242 CH—OCH₃ NH CH₃CN 2-Methylphenyl 243 CH—OCH₃ NH CH₃ CN 4-tert.-Butylphenyl 244 CH—OCH₃NH CH₃ CN 4-(n-Butoxyiminomethyl) phenyl 245 CH—OCH₃ NH CH₃ CN 2-Pyridyl246 CH—OCH₃ NH CH₃ CN Styryl 247 CH—OCH₃ NH CH₃ CN 1-Propenyl 248 N—OCH₃NH CH₃ CH₃ 3-Chlorphenyl m.p.: 71-74° C.; 249 N—OCH₃ NH CH₃ CH₃3,5-Dichlorphenyl m.p.: 94-97° C.; 250 N—OCH₃ NH CH₃ CH₃2,3,4-Trichlorphenyl m.p.: 110-112° C.; 251 N—OCH₃ NH CH₃ CH₃3-Bromphenyl m.p.: 74-77° C.; 252 N—OCH₃ NH CH₃ CH₃ 4-Methylphenyl m.p.:69-72° C.; 253 N—OCH₃ NH CH₃ CH₃ 4-Nitrophenyl m.p.: 134-137° C.; 254CH—CH₃ O CH₃ CN 2-Ethoxy-prop-2-yl IR film): 2982, 1717, 1436, 1255,1210, 1192, 1067, 1037, 1010 255 CH—CH₃ O CH₃ CN 2-i-Propoxy-prop-2-ylIR(film): 2983, 1718, 1383, 1370, 1244, 1173, 1119, 1109, 1037, 1002 256CH—CH₃ O CH₃ CN 2-n-Butoxy-prop-2-yl IR(film): 2957, 1718, 1435, 1255,1176, 1036, 1010, 759 257 CH—CH₃ O CH₃ CN 2-i-Butoxy-prop-2-yl IR(film):2956, 1717, 1435, 1366, 1255, 1209, 1176, 1064, 1037, 1008 258 CH—CH₃ OCH₃ CN Cyclopropyl ¹H-NMR(CDClhd 3): δ = 0.9m, 1.6d, 2.3m, 3.67s, 5.15s,7.05-7.4m 259 CH—CH₃ O CH₃ CN 2-Ethylthio-prop-2-yl ¹H-NMR(CDCl₃): δ =0.9m, 1.6d, 2.3m, 3.67s, 5.15s, 7.05-7.5m 260 CH—CH₃ O CH₃ CN2-i-Propylthio-pro-2-yl ¹H-NMR(CDCl₃): δ=1.15s, 1.5s, 1.6, 2.6m, 3.7s,5.1s, 7.1-7.5m 261 CH—CH₃ O CH₃ CN 2-Tetrahydropyranyl ¹H-NMR(CDCl₃):δ=1.4-1.9m, 1.6d, 3.5m, 3.7s, 4.1m, 5.1s, 7.0-7.5m

TABLE IV

No. X Y R¹ R³ R⁴ Data 1 CH—OCH₃ O CH₃ CH₃ Phenyl 2 CH—OCH₃ O CH₃ CH₃3-Bromophenyl 3 CH—OCH₃ O CH₃ CH₃ 4-Phenoxyphenyl 4 CH—OCH₃ O CH₃ CH₃4-Cyclohexylphenyl 5 NOCH₃ O CH₃ CH₃ Phenyl 6 NOCH₃ O CH₃ CH₃3-Bromophenyl oil; IR (film): 1727, 1436, 1312, 1240, 1032 7 NOCH₃ O CH₃CH₃ 4-Phenoxyphenyl oil; IR (film): 1727, 1489, 1239, 1031, 683 8 NOCH₃O CH₃ CH₃ 4-Cyclohexylphenyl oil; IR (film): 2925, 1728, 1447, 1239,1164, 1077,1032 9 CHOCH₃ O CH₃ CN iso-Propyl oil; IR (film): 2970, 2220,1710, 1127 10 CHOCH₃ O CH₃ CN 2-Methoxyprop-2-yl oil; IR (film): 2980,2220, 1710, 1127 11 CHOCH₃ O CH₃ CN 2-Methylthioprop-2-yl oil; IR(film): 2980, 2220, 1709, 1127 12 CHOCH₃ O CH₃ CN 2-Tetrahydrofuranyloil; IR (film): 2945, 2850, 2220, 1709, 1127 13 CHOCH₃ O CH₃ CN Phenyloil; IR (film): 2940, 2220, 1709, 1127, 1030

TABLE V

No. R³ R⁴ Data 1 H H 2 H Methoxymethyl 3 H Ethoxymethyl 4 Hn-Propoxymethyl 5 H iso-Propoxymethyl 6 H tert.-Butoxymethyl 7 H2-Methoxyprop-2-yl 8 H 2-Ethoxyprop-2-yl 9 H 2-n-Propoxyprop-2-yl 10 H2-iso-Propoxyprop-2-yl 11 H 2-tert.-Butoxyprop-2-yl 12 HMethylthiomethyl 13 H tert.-Butylthiomethyl 14 H 2-Methylthioprop-2-yl15 H 2-iso-Propylthioprop-2-yl 16 H 2-tert.-Butylthioprop-2-yl 17 HMethyl 18 H Ethyl 19 H n-Propyl 20 H iso-Propyl 21 H n-Butyl 22 Hiso-Butyl 23 H sec.-Butyl 24 H tert.-Butyl 25 H n-Hexyl 26 H n-Decyl 27H Cyclopropyl 28 H Cyclohexyl 29 H Phenylthiomethyl 30 H2-Phenylthiomethyl 31 H 2-(2′-Chlorophenylthio)prop-2-yl 32 H Ethynyl 33H 1-Propynyl 34 H Methoxy 35 H Ethoxy 36 H n-Propoxy 37 H iso-Propoxy 38H n-Butoxy 39 H iso-Butoxy 40 H sec.-Butoxy 41 H tert.-Butoxy 42 HMethylthio 43 H Ethylthio 44 H n-Propylthio 45 H iso-Propylthio 46 Hn-Butylthio 47 H iso-Butylthio 48 H sec.-Butylthio 49 H tert.-Butylthio50 H Benzylthio 51 H Trifluoromethoxy 52 H Cyano 53 H Amino 54 HMethylamino 55 H Dimethylamino 56 H Ethylamino 57 H Diethylamino 58 HDi-n-Propylamino 59 H Di-iso-Propylamino 60 H Di-n-Butylamino 61 HDi-iso-Butylamino 62 H Acetyl 63 H Propion-1-yl 64 H Butyr-1-yl 65 Hiso-Butyr-1-yl 66 H Pivaloyl 67 H Benzoyl 68 H 4-Chlorobenzoyl 69 HBenzylcarbonyl 70 H Methoxycarbonyl 71 H Ethoxycarbonyl 72 Hn-Propoxycarbonyl 73 H iso-Propoxycarbonyl 74 H n-Butoxycarbonyl 75 Hiso-Butoxycarbonyl 76 H sec.-Butoxycarbonyl 77 H tert.-Butoxycarbonyl 78H n-Hexoxycarbonyl 79 H Phenoxycarbonyl 80 H 4-Chlorphenoxycarbonyl 81 HBenzyloxycarbonyl 82 H Aminocarbonyl 83 H Dimethylaminocarbonyl 84 HDiethylaminocarbonyl 85 H Di-iso-Propylaminocarbonyl 86 HPhenylaminocarbonyl 87 H N-Methyl-N-Phenylaminocarbonyl 88 H Phenyl 89 H2-Fluorophenyl m.p.: 69-71° C.; 90 H 3-Fluorophenyl m.p.: 74-77° C.; 91H 4-Fluorophenyl m.p.: 73-76° C.; IR (KBr): 1699, 1278, 1271, 1256, 122592 H Pentafluorophenyl m.p.: 94-96° C.; IR (KBr): 1704, 1527, 1494, 113393 H 2-Chlorophenyl ¹H-NMR(CDCl₃): δ = 3.70s, 3.82s, 5.15s, 7.15-7.40m,7.52m, 7.60s, 7.85m, 8.52s 94 H 3-Chlorophenyl m.p.: 48-50° C.; 95 H4-Chlorophenyl (v. Example 6) 96 H Pentachlorophenyl 97 H2,3-Dichlorophenyl m.p.: 103-105° C.; 98 H 2,4-Dichlorophenyl m.p.:94-96° C.; 99 H 2,5-Dichlorophenyl 100 H 2,6-Dichlorophenyl m.p.:118-120° C.; 101 H 3,4-Dichlorophenyl m.p.: 82-84° C.; 102 H3,5-Dichlorophenyl m.p.: 94-96° C.; 103 H 2,3,4-Trichlorophenyl 104 H2,3,5-Trichlorophenyl 105 H 2,3,6-Trichlorophenyl 106 H2,4,5-Trichlorophenyl 107 H 2,4,6-Trichlorophenyl 108 H3,4,5-Trichlorophenyl 109 H 2,3,4,6-Tetrachlorophenyl 110 H2,3,5,6-Tetrachlorophenyl 111 H 2-Bromophenyl m.p.: 85-87° C.; 112 H3-Bromophenyl ¹H-NMR (CDCl₃): δ = 3.68s, 3.79s, 5.13, 7.15-7.54m, 7.59s7.74s, 8.00s 113 H 4-Bromophenyl m.p.: 131-134° C.; 114 H2,4-Dibromophenyl 115 H 3-Brom-4-fluorophenyl 116 H3-Brom-4-methoxyphenyl 117 H 2-Iodophenyl 118 H 3-Iodophenyl 119 H4-Iodophenyl 120 H 2-Chloro-4-fluorophenyl m.p.: 112-115° C.; 121 H2-Chloro-5-fluorophenyl 122 H 2-Chloro-6-fluorophenyl m.p.: 80-82° C.;123 H 2-Chloro-4-bromophenyl 124 H 2-Bromo-4-chlorophenyl 125 H2-Bromo-4-fluorophenyl 126 H 3-Bromo-4-chlorophenyl 127 H3-Chloro-4-fluorophenyl 128 H 3-Fluoro-4-chlorophenyl 129 H2-Cyanophenyl 130 H 3-Cyanophenyl 131 H 4-Cyanophenyl 132 H2-Nitrophenyl 133 H 3-Nitrophenyl 134 H 4-Nitrophenyl m.p.: 147-155° C.;135 H 2-Methylphenyl m.p.: 57-59° C.; 136 H 3-Methylphenyl m.p.: 54-56°C.; 137 H 4-Methylphenyl m.p.: 86-88° C.; 138 H 2,4-Dimethylphenyl m.p.:75-77° C.; 139 H 2,6-Dimethylphenyl 140 H 3,4-Dimethylphenyl 141 H3,5-Dimethylphenyl 142 H 2,3,4-Trimethylphenyl 143 H2,3,5-Trimethylphenyl 144 H 2,3,6-Trimethylphenyl 145 H2,4,5-Trimethylphenyl 146 H 2,4,6-Trimethylphenyl 147 H3,4,5-Trimethylphenyl 148 H Pentamethylphenyl 149 H 2-Ethylphenyl 150 H3-Ethylphenyl 151 H 4-Ethylphenyl 152 H 3,5-Diethylphenyl 153 H2-n-Propylphenyl 154 H 3-n-Propylphenyl 155 H 4-n-Propylphenyl 156 H2-iso-Propylphenyl 157 H 3-iso-Propylphenyl 158 H 4-iso-Propylphenyl 159H 2,4-Di-iso-Propylphenyl 160 H 3,5-Di-iso-Propylphenyl 161 H4-n-Butylphenyl 162 H 4-sec.-Butylphenyl 163 H 4-iso-Butylphenyl 164 H4-tert.-Butylphenyl m.p.: 71-73° C. 165 H 3-tert.-Butylphenyl 166 H2-tert.-Butylphenyl 167 H 2,4-Di-tert.-Butylphenyl 168 H3,5-Di-tert.-Butylphenyl 169 H 4-n-Hexylphenyl 170 H 4-n-Dodecylphenyl171 H 2-Methyl-4-tert.-Butylphenyl 172 H 2-Methyl-6-tert.-Butylphenyl173 H 2-Methyl-4-iso-Propylphenyl 174 H 2-Methyl-4-cyclohexylphenyl 175H 2-Methyl-4-phenylphenyl 176 H 2-Methyl-4-benzylphenyl 177 H2-Methyl-4-phenoxyphenyl 178 H 2-Methyl-4-benzyloxyphenyl 179 H2-Methyl-3-chlorophenyl 180 H 2-Methyl-4-chlorophenyl 181 H2-Methyl-5-chlorophenyl 182 H 2-Methyl-6-chlorophenyl 183 H2-Methyl-4-fluorophenyl 184 H 2-Methyl-3-bromophenyl 185 H2-Methyl-4-bromophenyl 186 H 2-Methyl-3-methoxyphenyl 187 H2-Methyl-4-methoxyphenyl 188 H 2-Methyl-5-methoxyphenyl 189 H2-Methyl-6-methoxyphenyl 190 H 2-Methyl-4-iso-Propoxyphenyl 191 H2-Methyl-2,5-dimethoxyphenyl 192 H 2-Methoxyphenyl m.p.: 52-54° C. 193 H3-Methoxyphenyl ¹H-NMR (CDCl₃): δ = 3.65s, 3.76s, 3.80s, 5.12s,6.88-7.54m, 7.58s, 8.05s 194 H 4-Methoxyphenyl m.p.: 61-63° C. 195 H2,3-Dimethoxyphenyl 196 H 2,4-Dimethoxyphenyl m.p.: 70-72° C. 197 H2,5-Dimethoxyphenyl 198 H 2,6-Dimethoxyphenyl 199 H 3,4-Dimethoxyphenyl200 H 3,5-Dimethoxyphenyl m.p.: 79-82° C. 201 H 3,6-Dimethoxyphenyl 202H 2,3,4-Trimethoxyphenyl 203 H 2,3,5-Trimethoxyphenyl 204 H2,3,6-Trimethoxyphenyl 205 H 2,4,5-Trimethoxyphenyl 206 H2,4,6-Trimethoxyphenyl 207 H 3,4,5-Trimethoxyphenyl 208 H 2-Ethoxyphenyl209 H 3-Ethoxyphenyl ¹H-NMR (CDCl₃): δ = 1.39t, 3.67s, 3.80s, 4.02q,5.12s, 6.87-7.54m, 7.58s, 8.05s 210 H 4-Ethoxyphenyl m.p.: 93-94° C. 211H 2-iso-Propoxyphenyl 212 H 3-iso-Propoxyphenyl 213 H4-iso-Propoxyphenyl 214 H 3-tert.-Butoxyphenyl 215 H4-tert.-Butoxyphenyl ¹H-NMR (CDCl₃): δ = 1.36s, 3.68s, 3.78s, 5.09s,6.94-7.53m, 7.58s, 8.07s 216 H 2-Trifluoromethoxyphenyl 217 H3-Trifluoromethoxyphenyl 218 H 4-Trifluoromethoxyphenyl 219 H3-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl 220 H4-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl 221 H 2-Chloromethylphenyl 222 H3-Chloromethylphenyl 223 H 4-Chloromethylphenyl 224 H2-Trifluoromethylphenyl m.p.: 75-77° C. 225 H 3-Trifluoromethylphenyl226 H 4-Trifluoromethylphenyl m.p.: 111-114° C. 227 H2-(Methoxyiminomethyl)phenyl 228 H 3-(Methoxyiminomethyl)phenyl 229 H4-(Methoxyiminomethyl)phenyl 230 H 2-(Ethoxyiminomethyl)phenyl 231 H3-(Ethoxyiminomethyl)phenyl 232 H 4-(Ethoxyiminomethyl)phenyl 233 H2-(n-Propoxyiminomethyl)phenyl 234 H 3-(n-Propoxyiminomethyl)phenyl 235H 4-(n-Propoxyiminomethyl)phenyl 236 H 2-(iso-Propoxyiminomethyl)phenyl237 H 3-(iso-Propoxyiminomethyl)phenyl 238 H4-(iso-Propoxyiminomethyl)phenyl 239 H 2-(n-Butoxyiminomethyl)phenyl 240H 3-(n-Butoxyiminomethyl)phenyl 241 H 4-(n-Butoxyiminomethyl)phenyl 242H 2-(iso-Butoxyiminomethyl)phenyl 243 H 3-(iso-Butoxyiminomethyl)phenyl244 H 4-(iso-Butoxyiminomethyl)phenyl 245 H2-(tert.-Butoxyiminomethyl)phenyl 246 H3-(tert.-Butoxyiminomethyl)phenyl 247 H4-(tert.-Butoxyiminomethyl)phenyl 248 H 2-(n-Pentoxyiminomethyl)phenyl249 H 3-(n-Pentoxyiminomethyl)phenyl 250 H4-(n-Pentoxyiminomethyl)phenyl 251 H 2-(n-Hexoxyiminomethyl)phenyl 252 H3-(n-Hexoxyiminomethyl)phenyl 253 H 4-(n-Hexoxyiminomethyl)phenyl 254 H2-(Allyloxyiminomethyl)phenyl 255 H 3-(Allyloxyiminomethyl)phenyl 256 H4-(Allyloxyiminomethyl)phenyl 257 H 2-(Benzyloxyiminomethyl)phenyl 258 H3-(Benzyloxyiminomethyl)phenyl 259 H 4-(Benzyloxyiminomethyl)phenyl 260H 2-(Methoxyimino-1′-ethyl)phenyl 261 H 3-(Methoxyimino-1′-ethyl)phenyl262 H 4-(Methoxyimino-1′-ethyl)phenyl 263 H2-(Ethoxyimino-1′-ethyl)phenyl 264 H 3-(Ethoxyimino-1′-ethyl)phenyl 265H 4-(Ethoxyimino-1′-ethyl)phenyl 266 H 2-(n-Propoxyimino-1′-ethyl)phenyl267 H 3-(n-Propoxyimino-1′-ethyl)phenyl 268 H4-(n-Propoxyimino-1′-ethyl)phenyl 269 H 2-(n-Butoxyamino-1′-ethyl)phenyl270 H 3-(n-Butoxyamino-1′-ethyl)phenyl 271 H4-(n-Butoxyamino-1′-ethyl)phenyl 272 H 2-(n-Pentoxyimino-1′-ethyl)phenyl273 H 3-(n-Pentoxyimino-1′-ethyl)phenyl 274 H4-(n-Pentoxyimino-1′-ethyl)phenyl 275 H 2-(n-Hexoxyimino-1′-ethyl)phenyl276 H 3-(n-Hexoxyimino-1′-ethyl)phenyl 277 H4-(n-Hexoxyimino-1′-ethyl)phenyl 278 H 2-(Allyloxyimino-1′-ethyl)phenyl279 H 3-(Allyloxyimino-1′-ethyl)phenyl 280 H4-(Allyloxyimino-1′-ethyl)phenyl 281 H 2-(Benzyloxyimino-1′-ethyl)phenyl282 H 3-(Benzyloxyimino-1′-ethyl)phenyl 283 H4-(Benzyloxyimino-1′-ethyl)phenyl 284 H 2-Phenylphenyl 285 H3-Phenylphenyl 286 H 4-Phenylphenyl m.p.: 94-96° C. 287 H2-Phenoxyphenyl 288 H 3-Phenoxyphenyl 289 H 4-Phenoxyphenyl 290 H2-Benzyloxyphenyl 291 H 3-Benzyloxyphenyl 292 H 4-Benzyloxyphenyl m.p.:94-96° C. 293 H 4-(Imidazol-1′-yl)phenyl 294 H 4-(Piperazin-1′-yl)phenyl295 H 4-(Morpholin-1′-yl)phenyl 296 H 4-(Piperidin-1′-yl)phenyl 297 H4-(Pyridyl-2′-oxy)phenyl 298 H 2-Cyclopropylphenyl 299 H3-Cyclopropylphenyl 300 H 4-Cyclopropylphenyl 301 H 3-Cyclohexylphenyl302 H 4-Cyclohexylphenyl 303 H 4-Oxiranylphenyl 304 H4-(1′,3′-Dioxan-2′-yl)phenyl 305 H 4-(Tetrahydropyran-2-yloxy)phenyl 306H 1-Naphthyl 307 H 2-Naphthyl oil; IR (film): 1707, 1633, 1257, 1129,110 308 H 9-Anthryl 309 H 1-Naphtoxy 310 H 2-Naphtoxy 311 H 9-Anthroxy312 H Phenoxy 313 H 2-Chlorophenoxy 314 H 3-Chlorophenoxy 315 H4-Chlorophenoxy 316 H 4-Methylphenoxy 317 H 4-tert.-Butylphenoxy 318 H4-Methoxyphenoxy 319 H 4-Ethoxyphenoxy 320 H 4-tert.-Butoxyphenoxy 321 HPhenylthio 322 H 2-Chlorophenylthio 323 H 4-Chlorophenylthio 324 HBenzyl 325 H 2-Methylbenzyl 326 H 3-Methylbenzyl 327 H 4-Methylbenzyl328 H 4-tert.-Butylbenzyl 329 H 2-Chlorobenzyl 330 H 3-Chlorobenzyl 331H 4-Chlorobenzyl 332 H 2,4-Dichlorobenzyl 333 H 2,6-Dichlorobenzyl 334 H2,4,6-Trichlorobenzyl 335 H 2-Trifluoromethylbenzyl 336 H3-Trifluoromethylbenzyl 337 H 4-Trifluoromethylbenzyl 338 H2-Methoxybenzyl 339 H 4-Methoxybenzyl 340 H 4-tert.-Butoxybenzyl 341 H4-Phenoxybenzyl 342 H 1-Phenethyl 343 H 2-Phenethyl 344 H 1-Phenylpropyl345 H 2-Phenylpropyl 346 H 3-Phenylpropyl 347 H 2-Methyl-2-phenylpropyl348 H 2-Methyl-3-phenylpropyl 349 H 4-Phenylbutyl 350 H2-Phenyl-1-ethenyl 351 H 1-Phenyl-1-ethenyl 352 H 1-Phenyl-1-propenyl353 H 1-Phenyl-1-propen-2-yl 354 H 2,2-Diphenylethenyl 355 HPhenoxymethyl 356 H 2-Pyridyl 357 H 3-Pyridyl 358 H 4-Pyridyl 359 H2,6-Pyrimidinyl 360 H 1,5-Pyrimidinyl 361 H 2-Thienyl 362 H 3-Thienyl363 H 2-Furyl 364 H 3-Furyl 365 H 1-Pyrrolyl 366 H 1-Imidazolyl 367 H1,2,4-Triazolyl 368 H 1,3,4-Triazolyl 369 H 4-Thiazolyl 370 H2-Benzothiazolyl 371 H 2-Pyridyloxy 372 H 2-Pyrimidinyloxy 373 H2-Pyridylthio 374 H 2-Pyrimidinylthio 375 H 2-Benzothiazolylthio 376 HPhenylthiomethyl 377 H 2-Pyridylmethyl 378 H 3-Pyridylmethyl 379 HFurfuryloxy 380 H Thienylmethoxy 381 H 3-Isoxazolylmethoxy 382 H2-Oxazolylmethoxy 383 H 2-Pyridylmethoxy 384 H 2′-Furyl-2-ethenyl 385 H2′-Thienyl-2-ethenyl 386 H 3′-Pyridyl-2-ethenyl 387 H Oxiranyl 388 H1-Aziridinyl 389 H 1-Azetidinyl 390 H 1-Pyrrolidinyl 391 H2-Tetrahydrofuryl 392 H 2-Tetrahydropyranyl 393 H 3-Tetrahydropyranyl394 H 1-Piperidinyl 395 H 1-Morpholinyl 396 H 1-Piperazinyl 397 H1,3-Dioxan-2-yl 398 H 3-Tetrahydrothiopyranyl 399 H 2-Dihydropyranyloxy400 H 2-Tetrahydropyranyloxy 401 H CF₃ 402 H 2-Fluoroethyl 403 H2,2,2-Trifluoroethyl 404 H Pentafluoroethyl 405 H Chloromethyl 406 HDichloromethyl 407 H Trichloromethyl 408 H 2-Chloroethyl 409 H2,2,2-Trichloroethyl 410 H Pentachloroethyl 411 H Cyclopropyl 412 HCyclobutyl 413 H Cyclopentyl 414 H Cyclohexyl 415 H 1-Methylcyclopropyl416 H 2,2-Dimethylcyclopropyl 417 H 1-Methylcyclohexyl 418 H2,2-Difluorocyclopropyl 419 H 2,2-Dichlorocyclopropyl 420 H2,2-Dibromocyclopropyl 421 H 2,2-Dichloro-3-Methylcyclopropyl 422 H2,2,3,3-Tetrafluorocyclobutyl 423 H Ethenyl 424 H 1-Propenyl 425 H2-Methyl-1-propenyl 426 H 4-Methylpent-3-en-1-yl 427 H 2-Propenyl 428 H2-Butenyl 429 H 1-Methyl-2-propenyl 430 H 3-Methyl-2-butenyl 431 H2,2-Difluoroethenyl 432 H 2,2-Dichloroethenyl 433 H3,3,3-Trifluoropropenyl 434 H 3,3,3-Trichloropropenyl 435 H3-Chloro-2-propenyl 436 H Cyclopent-1-enyl 437 H Cyclopentadienyl 438 HCyclohex-1-enyl 439 H Pentafluorocyclopentadienyl 440 HPentachlorocyclopentadienyl 441 H 4-Dimethylaminophenyl m.p.: 90-92° C.442 H 4-n-Butoxyphenyl m.p.: 79-82° C.

TABLE VI

No. R³ R⁴ Data 1 H H m.p.: 94-95° C. 2 H Methoxymethyl 3 H Ethoxymethyl4 H n-Propoxymethyl 5 H iso-Propoxymethyl 6 H tert.-Butoxymethyl 7 H2-Methoxyprop-2-yl 8 H 2-Ethoxyprop-2-yl 9 H 2-n-Propoxyprop-2-yl 10 H2-iso-Propoxyprop-2-yl 11 H 2-tert.-Butoxyprop-2-yl 12 HMethylthiomethyl 13 H tert.-Butylthiomethyl 14 H 2-Methylthioprop-2-yl15 H 2-iso-Propylthioprop-2-yl 16 H 2-tert.-Butylthioprop-2-yl 17 HMethyl 18 H Ethyl 19 H n-Propyl 20 H iso-Propyl 21 H n-Butyl 22 Hiso-Butyl 23 H sec.-Butyl 24 H tert.-Butyl 25 H n-Hexyl 26 H n-Decyl 27H Cyclopropyl 28 H Cyclohexyl 29 H Phenylthiomethyl 30 H2-Phenylthiomethyl 31 H 2-(2′-Chlorophenylthio)prop-2-yl 32 H Ethynyl 33H 1-Propynyl 34 H Methoxy 35 H Ethoxy 36 H n-Propoxy 37 H iso-Propoxy 38H n-Butoxy 39 H iso-Butoxy 40 H sec.-Butoxy 41 H tert.-Butoxy 42 HMethylthio 43 H Ethylthio 44 H n-Propylthio 45 H iso-Propylthio 46 Hn-Butylthio 47 H iso-Butylthio 48 H sec.-Butylthio 49 H tert.-Butylthio50 H Benzylthio 51 H Trifluoromethoxy 52 H Cyano 53 H Amino 54 HMethylamino 55 H Dimethylamino 56 H Ethylamino 57 H Diethylamino 58 HDi-n-Propylamino 59 H Di-iso-Propylamino 60 H Di-n-Butylamino 61 HDi-iso-Butylamino 62 H Acetyl 63 H Propion-1-yl 64 H Butyr-1-yl 65 Hiso-Butyr-1-yl 66 H Pivaloyl 67 H Benzoyl 68 H 4-Chlorobenzoyl 69 HBenzylcarbonyl 70 H Methoxycarbonyl 71 H Ethoxycarbonyl 72 Hn-Propoxycarbonyl 73 H iso-Propoxycarbonyl 74 H n-Butoxycarbonyl 75 Hiso-Butoxycarbonyl 76 H sec.-Butoxycarbonyl 77 H tert.-Butoxycarbonyl 78H n-Hexoxycarbonyl 79 H Phenoxycarbonyl 80 H 4-Chlorophenoxycarbonyl 81H Benzyloxycarbonyl 82 H Aminocarbonyl 83 H Dimethylaminocarbonyl 84 HDiethylaminocarbonyl 85 H Di-iso-Propylaminocarbonyl 86 HPhenylaminocarbonyl 87 H N-Methyl-N-Phenylaminocarbonyl 88 H Phenylm.p.: 92-95° C. 89 H 2-Fluorophenyl m.p.: 92-95° C. 90 H 3-Fluorophenylm.p.: 58-60° C. 91 H 4-Fluorophenyl m.p.: 110-111° C. 92 HPentafluorophenyl m.p.: 118-120° C. 93 H 2-Chlorophenyl ¹H-NMR(CDCl₃): δ= 3.70s, 3.82s, 5.15s, 7.15-7.40m, 7.52m, 7.60s, 7.85m, 8.52s 94 H3-Chlorophenyl m.p.: 58-60° C. 95 H 4-Chlorophenyl m.p.: 146-148° C. 96H Pentachlorophenyl 97 H 2,3-Dichlorophenyl m.p.: 95-97° C. 98 H2,4-Dichlorophenyl m.p.: 58-62° C. 99 H 2,5-Dichlorophenyl 100 H2,6-Dichlorophenyl m.p.: 136-140° C. 101 H 3,4-Dichlorophenyl m.p.:94-97° C. 102 H 3,5-Dichlorophenyl m.p.: 88-91° C. 103 H2,3,4-Trichlorophenyl 104 H 2,3,5-Trichlorophenyl 105 H2,3,6-Trichlorophenyl 106 H 2,4,5-Trichlorophenyl 107 H2,4,6-Trichlorophenyl 108 H 3,4,5-Trichlorophenyl 109 H2,3,4,6-Tetrachlorophenyl 110 H 2,3,5,6-Tetrachlorophenyl 111 H2-Bromophenyl m.p.: 91-94° C. 112 H 3-Bromophenyl m.p.: 63-64° C. 113 H4-Bromophenyl m.p.: 145-147° C. 114 H 2,4-Dibromophenyl 115 H3-Bromo-4-Fluorophenyl 116 H 3-Bromo-4-Methoxyphenyl 117 H 2-Iodophenyl118 H 3-Iodophenyl 119 H 4-Iodophenyl 120 H 2-Chloro-4-Fluorophenylm.p.: 90-93° C. 121 H 2-Chloro-5-Fluorophenyl 122 H2-Chloro-6-Fluorophenyl m.p.: 111-113° C. 123 H 2-Chloro-4-Bromophenyl124 H 2-Bromo-4-Chlorophenyl 125 H 2-Bromo-4-Fluorophenyl 126 H3-Bromo-4-Chlorophenyl 127 H 3-Chloro-4-Fluorophenyl 128 H3-Fluoro-4-Chlorophenyl 129 H 2-Cyanophenyl 130 H 3-Cyanophenyl 131 H4-Cyanophenyl 132 H 2-Nitrophenyl 133 H 3-Nitrophenyl 134 H4-Nitrophenyl m.p.: 142-146° C. 135 H 2-Methylphenyl m.p.: 58-60° C. 136H 3-Methylphenyl m.p.: 70-72° C. 137 H 4-Methylphenyl m.p.: 99-102° C.138 H 2,4-Dimethylphenyl m.p.: 54-56° C. 139 H 2,6-Dimethylphenyl 140 H3,4-Dimethylphenyl 141 H 3,5-Dimethylphenyl 142 H 2,3,4-Trimethylphenyl143 H 2,3,5-Trimethylphenyl 144 H 2,3,6-Trimethylphenyl 145 H2,4,5-Trimethylphenyl 146 H 2,4,6-Trimethylphenyl 147 H3,4,5-Trimethylphenyl 148 H Pentamethylphenyl 149 H 2-Ethylphenyl 150 H3-Ethylphenyl 151 H 4-Ethylphenyl 152 H 3,5-Diethylphenyl 153 H2-n-Propylphenyl 154 H 3-n-Propylphenyl 155 H 4-n-Propylphenyl 156 H2-iso-Propylphenyl 157 H 3-iso-Propylphenyl 158 H 4-iso-Propylphenyl 159H 2,4-Di-iso-Propylphenyl 160 H 3,5-Di-iso-Propylphenyl 161 H4-n-Butylphenyl 162 H 4-sec.-Butylphenyl 163 H 4-iso-Butylphenyl 164 H4-tert.-Butylphenyl m.p.: 82-84° C. 165 H 3-tert.-Butylphenyl 166 H2-tert.-Butylphenyl 167 H 2,4-Di-tert.-Butylphenyl 168 H3,5-Di-tert.-Butylphenyl 169 H 4-n-Hexylphenyl 170 H 4-n-Dodecylphenyl171 H 2-Methyl-4-tert.-Butylphenyl 172 H 2-Methyl-6-tert.-Butylphenyl173 H 2-Methyl-4-iso-Propylphenyl 174 H 2-Methyl-4-Cyclohexylphenyl 175H 2-Methyl-4-Phenylphenyl 176 H 2-Methyl-4-Benzylphenyl 177 H2-Methyl-4-Phenoxyphenyl 178 H 2-Methyl-4-Benzyloxyphenyl 179 H2-Methyl-3-Chlorophenyl 180 H 2-Methyl-4-Chlorophenyl 181 H2-Methyl-5-Chlorophenyl 182 H 2-Methyl-6-Chlorophenyl 183 H2-Methyl-4-Fluorophenyl 184 H 2-Methyl-3-Bromophenyl 185 H2-Methyl-4-Bromophenyl 186 H 2-Methyl-3-Methoxyphenyl 187 H2-Methyl-4-Methoxyphenyl 188 H 2-Methyl-5-Methoxyphenyl 189 H2-Methyl-6-Methoxyphenyl 190 H 2-Methyl-4-iso-Propoxyphenyl 191 H2-Methyl-2,5-Dimethoxyphenyl 192 H 2-Methoxyphenyl m.p.: 65-68° C. 193 H3-Methoxyphenyl m.p.: 83-84° C. 194 H 4-Methoxyphenyl m.p.: 88-90° C.195 H 2,3-Dimethoxyphenyl 196 H 2,4-Dimethoxyphenyl m.p.: 90-93° C. 197H 2,5-Dimethoxyphenyl 198 H 2,6-Dimethoxyphenyl 199 H3,4-Dimethoxyphenyl m.p.: 70-72° C. 200 H 3,5-Dimethoxyphenyl m.p.:97-99° C. 201 H 3,6-Dimethoxyphenyl 202 H 2,3,4-Trimethoxyphenyl 203 H2,3,5-Trimethoxyphenyl 204 H 2,3,6-Trimethoxyphenyl 205 H2,4,5-Trimethoxyphenyl 206 H 2,4,6-Trimethoxyphenyl 207 H3,4,5-Trimethoxyphenyl m.p.: 105-109° C. 208 H 2-Ethoxyphenyl 209 H3-Ethoxyphenyl m.p.: 90-92° C. 210 H 4-Ethoxyphenyl m.p.: 97-98° C. 211H 2-iso-Propoxyphenyl 212 H 3-iso-Propoxyphenyl 213 H4-iso-Propoxyphenyl 214 H 3-tert.-Butoxyphenyl 215 H4-tert.-Butoxyphenyl m.p.: 78-83° C. 216 H 2-Trifluoromethoxyphenyl 217H 3-Trifluoromethoxyphenyl 218 H 4-Trifluoromethoxyphenyl 219 H3-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl 220 H4-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl 221 H 2-Chloromethylphenyl 222 H3-Chloromethylphenyl 223 H 4-Chloromethylphenyl 224 H2-Trifluoromethylphenyl m.p.: 58-60° C. 225 H 3-Trifluoromethylphenylm.p.: 74-77° C. 226 H 4-Trifluoromethylphenyl m.p.: 120-122° C. 227 H2-(Methoxyiminomethyl)phenyl 228 H 3-(Methoxyiminomethyl)phenyl 229 H4-(Methoxyiminomethyl)phenyl 230 H 2-(Ethoxyiminomethyl)phenyl 231 H3-(Ethoxyiminomethyl)phenyl 232 H 4-(Ethoxyiminomethyl)phenyl 233 H2-(n-Propoxyiminomethyl)phenyl 234 H 3-(n-Propoxyiminomethyl)phenyl 235H 4-(n-Propoxyiminomethyl)phenyl 236 H 2-(iso-Propoxyiminomethyl)phenyl237 H 3-(iso-Propoxyiminomethyl)phenyl 238 H4-(iso-Propoxyiminomethyl)phenyl 239 H 2-(n-Butoxyiminomethyl)phenyl 240H 3-(n-Butoxyiminomethyl)phenyl 241 H 4-(n-Butoxyiminomethyl)phenyl 242H 2-(iso-Butoxyiminomethyl)phenyl 243 H 3-(iso-Butoxyiminomethyl)phenyl244 H 4-(iso-Butoxyiminomethyl)phenyl 245 H2-(tert.-Butoxyiminomethyl)phenyl 246 H3-(tert.-Butoxyiminomethyl)phenyl 247 H4-(tert.-Butoxyiminomethyl)phenyl 248 H 2-(n-Pentoxyiminomethyl)phenyl249 H 3-(n-Pentoxyiminomethyl)phenyl 250 H4-(n-Pentoxyiminomethyl)phenyl 251 H 2-(n-Hexoxyiminomethyl)phenyl 252 H3-(n-Hexoxyiminomethyl)phenyl 253 H 4-(n-Hexoxyiminomethyl)phenyl 254 H2-(Allyloxyiminomethyl)phenyl 255 H 3-(Allyloxyiminomethyl)phenyl 256 H4-(Allyloxyiminomethyl)phenyl 257 H 2-(Benzyloxyiminomethyl)phenyl 258 H3-(Benzyloxyiminomethyl)phenyl 259 H 4-(Benzyloxyiminomethyl)phenyl 260H 2-(Methoxyimino-1′-ethyl)phenyl 261 H 3-(Methoxyimino-1′-ethyl)phenyl262 H 4-(Methoxyimino-1′-ethyl)phenyl 263 H2-(Ethoxyimino-1′-ethyl)phenyl 264 H 3-(Ethoxyimino-1′-ethyl)phenyl 265H 4-(Ethoxyimino-1′-ethyl)phenyl 266 H 2-(n-Propoxyimino-1′-ethyl)phenyl267 H 3-(n-Propoxyimino-1′-ethyl)phenyl 268 H4-(n-Propoxyimino-1′-ethyl)phenyl 269 H 2-(n-Butoxyamino-1′-ethyl)phenyl270 H 3-(n-Butoxyamino-1′-ethyl)phenyl 271 H4-(n-Butoxyamino-1′-ethyl)phenyl 272 H 2-(n-Pentoxyimino-1′-ethyl)phenyl273 H 3-(n-Pentoxyimino-1′-ethyl)phenyl 274 H4-(n-Pentoxyimino-1′-ethyl)phenyl 275 H 2-(n-Hexoxyimino-1′-ethyl)phenyl276 H 3-(n-Hexoxyimino-1′-ethyl)phenyl 277 H4-(n-Hexoxyimino-1′-ethyl)phenyl 278 H 2-(Allyloxyimino-1′-ethyl)phenyl279 H 3-(Allyloxyimino-1′-ethyl)phenyl 280 H4-(Allyloxyimino-1′-ethyl)phenyl 281 H 2-(Benzyloxyimino-1′-ethyl)phenyl282 H 3-(Benzyloxyimino-1′-ethyl)phenyl 283 H4-(Benzyloxyimino-1′-ethyl)phenyl 284 H 2-Phenylphenyl 285 H3-Phenylphenyl 286 H 4-Phenylphenyl m.p.: 100-102° C. 287 H2-Phenoxyphenyl 288 H 3-Phenoxyphenyl IR (film): 1728, 1489, 1247, 1214,1070, 1020 289 H 4-Phenoxyphenyl m.p.: 85-87° C. 290 H 2-Benzyloxyphenylm.p.: 83-85° C. 291 H 3-Benzyloxyphenyl m.p.: 66-68° C. 292 H4-Benzyloxyphenyl m.p.: 104-106° C. 293 H 4-(Imidazol-1′-yl)phenyl 294 H4-(Piperazin-1′-yl)phenyl 295 H 4-(Morpholin-1′-yl)phenyl 296 H4-(Piperidin-1′-yl)phenyl 297 H 4-(Pyridyl-2′-oxy)phenyl 298 H2-Cyclopropylphenyl 299 H 3-Cyclopropylphenyl 300 H 4-Cyclopropylphenyl301 H 3-Cyclohexylphenyl 302 H 4-Cyclohexylphenyl 303 H 4-Oxiranylphenyl304 H 4-(1′,3′-Dioxan-2′-yl)phenyl 305 H4-(Tetrahydropyran-2-yloxy)phenyl 306 H 1-Naphthyl m.p.: 70-73° C. 307 H2-Naphthyl m.p.: 125-126° C. 308 H 9-Anthryl 309 H 1-Naphthoxy 310 H2-Naphthoxy 311 H 9-Anthroxy 312 H Phenoxy 313 H 2-Chlorophenoxy 314 H3-Chlorophenoxy 315 H 4-Chlorophenoxy 316 H 4-Methylphenoxy 317 H4-tert.-Butylphenoxy 318 H 4-Methoxyphenoxy 319 H 4-Ethoxyphenoxy 320 H4-tert.-Butoxyphenoxy 321 H Phenylthio 322 H 2-Chlorophenylthio 323 H4-Chlorophenylthio 324 H Benzyl 325 H 2-Methylbenzyl 326 H3-Methylbenzyl 327 H 4-Methylbenzyl 328 H 4-tert.-Butylbenzyl 329 H2-Chlorobenzyl 330 H 3-Chlorobenzyl 331 H 4-Chlorobenzyl 332 H2,4-Dichlorobenzyl 333 H 2,6-Dichlorobenzyl 334 H 2,4,6-Trichlorobenzyl335 H 2-Trifluoromethylbenzyl 336 H 3-Trifluoromethylbenzyl 337 H4-Trifluoromethylbenzyl 338 H 2-Methoxybenzyl 339 H 4-Methoxybenzyl 340H 4-tert.-Butoxybenzyl 341 H 4-Phenoxybenzyl 342 H 1-Phenethyl 343 H2-Phenethyl 344 H 1-Phenylpropyl 345 H 2-Phenylpropyl 346 H3-Phenylpropyl 347 H 2-Methyl-2-phenylpropyl 348 H2-Methyl-3-phenylpropyl 349 H 4-Phenylbutyl 350 H 2-Phenyl-1-ethenyl 351H 1-Phenyl-1-ethenyl 352 H 1-Phenyl-1-propenyl 353 H1-Phenyl-1-propen-2-yl 354 H 2,2-Diphenylethenyl 355 H Phenoxymethyl 356H 2-Pyridyl 357 H 3-Pyridyl 358 H 4-Pyridyl 359 H 2,6-Pyrimidinyl 360 H1,5-Pyrimidinyl 361 H 2-Thienyl 362 H 3-Thienyl 363 H 2-Furyl 364 H3-Furyl 365 H 1-Pyrrolyl 366 H 1-Imidazolyl 367 H 1,2,4-Triazolyl 368 H1,3,4-Triazolyl 369 H 4-Thiazolyl 370 H 2-Benzothiazolyl 371 H2-Pyridyloxy 372 H 2-Pyrimidinyloxy 373 H 2-Pyridylthio 374 H2-Pyrimidinylthio 375 H 2-Benzothiazolylthio 376 H Phenylthiomethyl 377H 2-Pyridylmethyl 378 H 3-Pyridylmethyl 379 H Furfuryloxy 380 HThienylmethoxy 381 H 3-Isoxazolylmethoxy 382 H 2-Oxazolylmethoxy 383 H2-Pyridylmethoxy 384 H 2′-Furyl-2-ethenyl 385 H 2′-Thienyl-2-ethenyl 386H 3′-Pyridyl-2-ethenyl 387 H Oxiranyl 388 H 1-Aziridinyl 389 H1-Azetidinyl 390 H 1-Pyrrolidinyl 391 H 2-Tetrahydrofuryl 392 H2-Tetrahydropyranyl 393 H 3-Tetrahydropyranyl 394 H 1-Piperidinyl 395 H1-Morpholinyl 396 H 1-Piperazinyl 397 H 1,3-Dioxan-2-yl 398 H3-Tetrahydrothiopyranyl 399 H 2-Dihydropyranyloxy 400 H2-Tetrahydropyranyloxy 401 H CF₃ 402 H 2-Fluoroethyl 403 H2,2,2-Trifluoroethyl 404 H Pentafluoroethyl 405 H Chloromethyl 406 HDichloromethyl 407 H Trichloromethyl 408 H 2-Chloroethyl 409 H2,2,2-Trichloroethyl 410 H Pentachloroethyl 411 H Cyclopropyl 412 HCyclobutyl 413 H Cyclopentyl 414 H Cyclohexyl 415 H 1-Methylcyclopropyl416 H 2,2-Dimethylcyclopropyl 417 H 1-Methylcyclohexyl 418 H2,2-Difluorocyclopropyl 419 H 2,2-Dichlorocyclopropyl 420 H2,2-Dibromocyclopropyl 421 H 2,2-Dichloro-3-methylcyclopropyl 422 H2,2,3,3-Tetrafluorocyclobutyl 423 H Ethenyl 424 H 1-Propenyl 425 H2-Methyl-1-propenyl 426 H 4-Methylpent-3-en-1-yl 427 H 2-Propenyl 428 H2-Butenyl 429 H 1-Methyl-2-propenyl 430 H 3-Methyl-2-butenyl 431 H2,2-Difluoroethenyl 432 H 2,2-Dichloroethenyl 433 H3,3,3-Trifluoropropenyl 434 H 3,3,3-Trichloropropenyl 435 H3-Chloro-2-propenyl 436 H Cyclopent-1-enyl 437 H Cyclopentadienyl 438 HCyclohex-1-enyl 439 H Pentafluorocyclopentadienyl 440 HPentachlorocyclopentadienyl 441 H 4-Dimethylaminophenyl m.p.: 70-71° C.442 H 4-Allyloxyphenyl m.p.: 81-83° C. 443 H Diphenylmethyl m.p.: 66-68°C. 444 H Dimethylbenzyl ¹H-NMR (CDCl₃): δ = 1.45S 3.78s, 4.03s, 5.00s7.17-7.41m

TABLE VII

No. R_(n) ⁸ Data 1 H m.p. 156-158° C. 2 3-Fluoro 3 4-Fluoro 4 3-Chloro 54-Chloro 6 3-Bromo 7 4-Bromo 8 3-Iodo 9 4-Iodo 10 3,4-Dichloro 113,5-Dichloro 12 3,6-Dichloro 13 4,5-Dichloro 14 3,4,5-Trichloro 153,4,6-Trichloro 16 3,4,5,6-Tetrachloro 17 3,4,5,6-Tetrafluoro 183,4,5,6-Tetrabromo 19 3,5-Difluoro 20 3,5-Dibromo 21 3-Methyl 224-Methyl 23 3-Ethyl 24 4-Ethyl 25 3-iso-Propyl 26 4-iso-Propyl 273-tert-Butyl 28 4-tert-Butyl 29 3,4-Dimethyl 30 3,5-Dimethyl 313,6-Dimethyl 32 4,5-Dimethyl 33 3,4,5-Trimethyl 34 3,4,6-Trimethyl 353,4,5,6-Tetramethyl 36 3-Nitro 37 4-Nitro 38 3,5-Dinitro 39 3-Cyano 404-Cyano 41 3-Methoxy 42 4-Methoxy 43 3-tert.Butoxy 44 4-tert.Butoxy 453-Trifluoromethyl 46 4-Trifluoromethyl 47 3-Chloromethyl 484-Chloromethyl 49 3-Trifluoromethoxy 50 4-Trifluoromethoxy 513-Benzyloxy 52 4-Benzyloxy 53 4,5-Dibenzyloxy 54 3-Phenoxy 55 4-Phenoxy56 3-Phenyl 57 4-Phenyl 58 3-Pyrid-2′-yl 59 4-Pyrid-2′-yl 603-Pyrid-2′-yloxy 61 4-Pyrid-2′-yloxy

TABLE VIII

No. R_(n) ⁸ Data 1 H m.p. 152-155° C. 2 3-Fluoro 3 4-Fluoro 4 3-Chloro 54-Chloro 6 3-Bromo 7 4-Bromo 8 3-Iodo 9 4-Iodo 10 3,4-Dichloro 113,5-Dichloro 12 3,6-Dichloro 13 4,5-Dichloro 14 3,4,5-Trichloro 153,4,6-Trichloro 16 3,4,5,6-Tetrachloro 17 3,4,5,6-Tetrafluoro 183,4,5,6-Tetrabromo 19 3,5-Difluoro 20 3,5-Dibromo 21 3-Methyl 224-Methyl 23 3-Ethyl 24 4-Ethyl 25 3-iso-Propyl 26 4-iso-Propyl 273-tert-Butyl 28 4-tert-Butyl 29 3,4-Dimethyl 30 3,5-Dimethyl 313,6-Dimethyl 32 4,5-Dimethyl 33 3,4,5-Trimethyl 34 3,4,6-Trimethyl 353,4,5,6-Tetramethyl 36 3-Nitro 37 4-Nitro 38 3,5-Dinitro 39 3-Cyano 404-Cyano 41 3-Methoxy 42 4-Methoxy 43 3-tert.Butoxy 44 4-tert.Butoxy 453-Trifluoromethyl 46 4-Trifluoromethyl 47 3-Chloromethyl 484-Chloromethyl 49 3-Trifluoromethoxy 50 4-Trifluoromethoxy 513-Benzyloxy 52 4-Benzyloxy 53 4,5-Dibenzyloxy 54 3-Phenoxy 55 4-Phenoxy56 3-Phenyl 57 4-Phenyl 58 3-Pyrid-2′-yl 59 4-Pyrid-2′-yl 603-Pyrid-2′-yloxy 61 4-Pyrid-2′-yloxy

TABLE IX

No. X Y R¹ R⁸ Data 1 CH—SCH₃ O CH₃ H 2 CH—SCH₃ NH CH₃ H 3 CH—SCH₃ S CH₃H 4 CH₂ O CH₃ H 5 CH₂ NH CH₃ H 6 CH₂ S CH₃ H 7 CH—CH₃ O CH₃ H 8 CH—CH₃NH CH₃ H 9 CH—CH₃ S CH₃ H 10 CH—CH₃ O CH₃ Perchloro 11 CH—CH₃ NH CH₃Perchloro 12 CH—CH₃ S CH₃ Perchloro 13 CH—OCH₃ NH CH₃ H 14 CH—OCH₃ S CH₃H 15 CH—OCH₃ NH CH₃ Perchloro 16 CH—OCH₃ S CH₃ Perchloro 17 N—OCH₃ NHCH₃ H 18 N—OCH₃ S CH₃ H 19 N—OCH₃ NH CH₃ Perchloro 20 N—OCH₃ S CH₃Perchloro

In general terms, the novel compounds are extremely effective on a broadspectrum of phytopathogenic fungi, in particular those from the classconsisting of the Ascomycetes and Basidiomycetes. Some of them have asystemic action and can be used as foliar and soil fungicides.

The fungicidal compounds are of particular interest for controlling alarge number of fungi in various crops or their seeds, especially wheat,rye, barley, oats, rice, Indian corn, lawns, cotton, soybeans, coffee,sugar cane, fruit and ornamentals in horticulture and viticulture, andin vegetables such as cucumbers, beans and cucurbits.

The novel compounds are particularly useful for controlling thefollowing plant diseases:

Erysiphe graminis in cereals,

Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,

Podosphaera leucotricha in apples,

Uncinula necator in vines,

Puccinia species in cereals,

Rhizoctonia solani in cotton,

Ustilago species in cereals and sugar cane,

Venturia inaequalis (scab) in apples,

Helminthosporium species in cereals,

Septoria nodorum in wheat,

Botrytis cinerea (gray mold) in strawberries and grapes,

Cercospora arachidicola in groundnuts,

Pseudocercosporella herpotrichoides in wheat and barley,

Pyricularia oryzae in rice,

Phytophthora infestans in potatoes and tomatoes,

Fusarium and Verticillium species in various plants,

Plasmopara viticola in grapes,

Alternaria species in fruit and vegetables.

The compounds are applied by spraying or dusting the plants with theactive ingredients, or treating the seeds of the plants with the activeingredients. They may be applied before or after infection of the plantsor seeds by the fungi. Either the fungi themselves, or the plants, seedor materials to be protected against fungus attack, or the soil aretreated with a fungicidally effective amount of the active ingredient.

The novel substances can be converted into conventional formulationssuch as solutions, emulsions, suspensions, dusts, powders, pastes andgranules. The application forms depend entirely on the purposes forwhich they are intended; they should at all events ensure a fine anduniform distribution of the active ingredient. The formulations areproduced in known manner, for example by extending the active ingredientwith solvents and/or carriers, with or without the use of emulsifiersand dispersants; if water is used as solvent, it is also possible toemploy other organic solvents as auxiliary solvents. Suitableauxiliaries for this purpose are solvents such as aromatics (e.g.,xylene), chlorinated aromatics (e.g., chlorobenzenes), paraffins (e.g.,crude oil fractions), alcohols (e.g., methanol, butanol), ketones (e.g.,cyclohexanone), amines (e.g., ethanolamine, dimethylformamide), andwater; carriers such as ground natural minerals (e.g., kaolins,aluminas, talc and chalk) and ground synthetic minerals (e.g., highlydisperse silica and silicates); emulsifiers such as nonionic and anionicemulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkylsulfonates and aryl sulfonates); and dispersants such as ligninsulfitewaste liquors and methylcellulose.

The fungicides generally contain from 0.1 to 95, and preferably from 0.5to 90, wt % of active ingredient. The application rates are from 0.02 to3 kg or more of active ingredient per hectare, depending on the type ofeffect desired. The novel compounds may also be used for protectingmaterials, e.g., on Paecilomyces variotii. When the active ingredientsare used for treating seed, amounts of from 0.001 to 50, and preferablyfrom 0.01 to 10, g per kg of seed are generally required.

The agents and the ready-to-use formulations prepared from them, such assolutions, emulsions, suspensions, powders, dusts, pastes and granules,are applied in conventional manner, for example by spraying, atomizing,dusting, scattering, dressing or watering.

Examples of formulations are given below.

I. A solution of 90 parts by weight of compound no. 429 (Table I) and 10parts by weight of N-methyl-α-pyrrolidone, which is suitable forapplication in the form of very fine drops.

II. A mixture of 20 parts by weight of compound no. 14 (Table II), 80parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 moleof castor oil. By finely dispersing the mixture in water, an aqueousdispersion is obtained.

III. An aqueous dispersion of 20 parts by weight of compound no. 49(Table I), 40 parts by weight of cyclohexanone, 30 parts by weight ofisobutanol, 20 parts by weight of the adduct of 40 moles of ethyleneoxide and 1 mole of castor oil. By finely dispersing the solution inwater, an aqueous dispersion is obtained.

IV. An aqueous dispersion of 20 parts by weight of compound no. 56(Table I), 25 parts by weight of cyclohexanol, 65 parts by weight of amineral oil fraction having a boiling point between 210 and 280° C., and10 parts by weight of the adduct of 40 moles of ethylene oxide and 1mole of castor oil. By finely distributing the solution in water, anaqueous dispersion is obtained.

V. A hammer-milled mixture of 80 parts by weight of compound no. 14(Table I), 3 parts by weight of the sodium salt ofdiisobutylnaphthalene-α-sulfonic acid, 10 parts by weight of the sodiumsalt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and7 parts by weight of powdered silica gel. By finely dispersing themixture in water, a spray liquor is obtained.

VI. An intimate mixture of 3 parts by weight of compound no. 17 (TableII) and 97 parts by weight of particulate kaolin. The dust contains 3 wt% of the active ingredient.

VII. An intimate mixture of 30 parts by weight of compound no. 17 (TableI), 92 parts by weight of powdered silica gel and 8 parts by weight ofparaffin oil sprayed onto the surface of this silica gel. Thisformulation of the active ingredient exhibits good adherence.

VIII. A stable aqueous dispersion of 40 parts by weight of compound no.571 (Table I), 10 parts of the sodium salt of a phenolsulfonicacid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts byweight of water, which dispersion can be further diluted.

IX. A stable oily dispersion of 20 parts by weight of compound no. 616(Table I), 2 parts by weight of the calcium salt ofdodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcoholpolyglycol ether, 2 parts by weight of the sodium salt of aphenolsulfonic acid-urea-formaldehyde condensate and 68 parts by weightof a paraffinic mineral oil.

In these application forms, the agents according to the invention mayalso be present together with other active ingredients, for exampleherbicides, insecticides, growth regulators, and fungicides, and mayfurthermore be mixed and applied together with fertilizers. Admixturewith other fungicides frequently results in a greater fungicidal actionspectrum.

Use Examples

The active ingredient used for comparison purposes was2-(phenoxymethyl)-phenylglyoxylic acid-methyl ester-O-methyloxime (A)disclosed in EP 253,213.

Use Example 1

Action on Wheat Brown Rust

Leaves of pot-grown wheat seedlings of the “Kanzler” variety were dustedwith spores of brown rust (Puccinia recondita). The pots were thenplaced for 24 hours at 20 to 22° C. in a high-humidity (90-95%) chamber.During this period the spores germinated and the germ tubes penetratedthe leaf tissue. The infected plants were then sprayed to runoff withaqueous liquors containing (dry basis) 80% of active ingredient and 20%of emulsifier. After the sprayed-on layer had dried, the plants were setup in the greenhouse at 20 to 22° C. and a relative humidity of 65 to70%. The extent of rust fungus spread on the leaves was assessed after 8days.

The results show that active ingredients nos. 49, 429, 56, 14, 15, 16,17, 582, 578, 573, 592, 571, 704, 705 and 616 from Table I and nos. 17and 644 from Table II, applied as 0.025 wt % spray liquors, have abetter fungicidal action (95%) than prior art comparative compound A(50%).

Use Example 2

Action on Pyricularia oryzae (Protective)

Leaves of pot-grown rice seedlings of the “Bahia” variety were sprayedto runoff with aqueous emulsions containing (dry basis) 80% of activeingredient and 20% of emulsifier, and inoculated 24 hours later with anaqueous spore suspension of Pyricularia oryzae. The plants were then setup in climatic cabinets at 22 to 24° C. and 95 to 99% relative humidity.The extent of fungus attack was assessed after 6 days.

The results show that active ingredients nos. 429, 583, 593, 592, 571,706 and 616 from Table I and nos. 14, 15, 16, 17, 582, 592, 571, 769,782, 672, 644 and 583 from Table II, applied as 0.05 wt % spray liquors,have a very good fungicidal action (100%).

The novel compounds are also suitable for effectively combating pestssuch as insects, arachnids and nematodes. They may be used as pesticidesin crop protection and in the hygiene, stores protection and veterinarysector.

Examples of injurious insects belonging to the Lepidoptera order areAgrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsiagemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius,Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneurafumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydiapomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella,Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella,Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitafunebrana, Grapholita molesta, Heliothis armigera, Heliothis virescens,Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea,Hyponomeuta malinellus, Keifferia lycopersicella, Lambdina fiscellaria,Laphygma exigua, Leucoptera coffeella, Leucoptera scitella,Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis,Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosomaneustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis,Panolis flamea, Pectinophora gossypiella, Peridroma saucia, Phalerabucephala, Phthorimaea operculella, Phyllocnistis citrella, Pierisbrassicae, Plathypena scarbra, Plutella xylostella, Pseudoplusiaincludens, Phyacionia frustrana, Scrobipalpula absoluta, Sitotrogacerelella, Sparganothis pilleriana, Spodoptera frugiperda, Spodopteralittoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrixviridana, Trichoplusia ni and Zeiraphera canadensis.

Examples from the Coleoptera order are Agrilus sinuatus, Agrioteslineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrusdispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis,Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchuspisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotomatrifurcata, Ceuthorrhynchus assimilis, Ceuthorrynchus napi, Chaetocnematibialis, Conoderus vespertinus, Crioceris asparagi, Diabroticalongicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachnavarivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobiusabietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lemabilineata, Lema melanopus, Leptinotarsa decemlineata, Limoniuscalifornicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethesaeneus, Melolontha hippocastani, Melolontha melolontha, Onlema oryzae,Ortiorrhynchus sulcatus, Ortiorrhynchus ovatus, Phaedon cochleariae,Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola,Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitonalineatus and Sitophilus granaria.

Examples from the Diptera order are Aedes aegypti, Aedes vexans,Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomyabezziana, Chrysomya hominivorax, Chrysomya macellaria, Contariniasorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae,Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilusintestinalis, Glossia morsitans, Haematobia irritans, Haplodiplosisequestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae,Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata,Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscinastabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbiaantiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi,Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea and Tipulapaludosa.

Examples from the Thysanoptera order are Frankliniella fusca,Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri,Thrips oryzae, Thrips palmi and Thrips tabaci.

Examples from the Hymenoptera order are Athalia rosae, Atta cephalotes,Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea,Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta.

Examples from the Heteroptera order are Acrosternum hilare, Blissusleucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercusintermedius, Eurygaster integriceps, Euchistus impictiventris,Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezaraviridula, Piesma quadrata, Solubea insularis and Thyanta perditor.

Examples from the nematodes class are root-knot nematodes, e.g.,Meloidogyne hapla, Meloidogyne incognita and Meloidogyne javanica,cyst-forming nematodes, e.g., Globodera rostochiensis, Heteroderaavenae, Hetrodera glycinae, Heterodera schachtii and Heteroderatrifolii, and stem and leaf eelworms, e.g., Belonolaimus longicaudatus,Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchusmulticinctus, Longidorus elongatus, Radopholus similis, Rotylenchusrobustus, Trichodorus primitivus, Tylenchorhynchus claytoni,Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans,Pratylenchus curvitatus and Pratylenchus goodeyi.

When the active ingredients are used for combating pests, theconcentrations in the finished formulations may vary over a wide range.Generally, the concentration is from 0.0001 to 10, and preferably from0.001 to 0.1,%.

The active ingredients may also be successfully used in theultra-low-volume method (ULV), where it is possible to applyformulations containing more than 95 wt % of active ingredient, or eventhe active ingredient without any additives.

When the active ingredients are used for combating pests in the open,the application rates are from 0.01 to 10, and preferably from 0.1 to1.0, kg/ha.

Use Example 3

Tetranychus telarius (Spider Mite); Contact Action—Spray Test

Potted bush beans which had developed the first pair of true leaves andwere heavily infested with all stages of the spider mite Tetranychustelarius were sprayed to runoff in a spray cabinet with aqueousformulations of the active ingredients. The plants were placed on arotating disc and sprayed from all sides with 50 ml of spray liquor. Theplants were heavily infested with mites and numerous eggs had been laidon them. The action was assessed after 5 days by means of a binocularmicroscope. During this period, the plants were kept under normalgreenhouse conditions.

Application rate Mortality in ppm in % Compound no. from Table I  49 10080  36 100 80  43 1000 100 429 1000 100  38 40 100  39 100 100  45 1000100 582 about 20 100 579 20 80 583 40 100 573 20 100 593 1000 80 592 40100 704 about 20 100 705 40 100 Compound no. from Table II  37 1000 100 39 1000 100  45 1000 100

Use Example 4

Musca domestica (Housefly); Continuous Contact Action

Both the tops and bottoms of Petri dishes 10 cm in diameter were linedwith a total of 1 ml of acetonic solutions of the active ingredients.After the solvent had evaporated (about 30 mins.), 10 flies andabsorbent cotton steeped in water were introduced into each dish and thedishes closed. The flies in supine position were counted after 24 hours.

If a kill rate of 80 to 100% occurs at a concentration of 0.01 mg/dish,the test is continued with falling concentrations.

Compound no. Application rate Mortality from Table I in mg in % 49 0.180 36 1.0 80 37 0.1 100 582 0.1 80 593 0.1 60 705 0.1 100 706 0.1 100

Use Example 5

Plutella maculipennis (Diamondback Moth); Ingestion-inhibiting Action

Young kohlrabi leaves are dipped for 3 seconds into aqueous solutions ofthe candidate compounds, and then placed on a round filter paper 9 cm indiameter which has been moistened with 0.5 ml of water. The filter paperis then placed in a Petri dish 10 cm in diameter. 10 caterpillars in the4th larval stage are then placed on each leaf, and the Petri dish isclosed. Ingestion inhibition is determined in % after 48 hours.

Compound no. Application rate Mortality from Table I in ppm in % 49 20080 36 200 80 429 1000 80 16 400 80 582 400 100 593 1000 80 592 400 80705 400 80 706 400 80

Use Example 6

Action on Peronospora in Grapes

Leaves of potted vines of the “Müller Thurgau” variety were sprayed withaqueous liquors containing (dry basis) 80% of active ingredient and 20%of emulsifier. To assess the duration of action of the activeingredients, the plants were, after the sprayed-on layer had dried, setup in the greenhouse for 8 days. Only then were the leaves infected witha zoospore suspension of Plasmopara viticola. The vines were then placedfor 48 hours in a water-vapor-saturated chamber at 24° C. and then for 5days in a greenhouse at from 20 to 30° C. To accelerate thesporangiophore discharge, the plants were then again set up in the moistchamber for 16 hours. The extent to which the leaves had been attackedwas then assessed.

The results show that active ingredients nos. 49, 429, 56, 14, 15, 16,17, 582, 578, 573, 592, 571, 704, 705, 616, 117, 156, 579, 583, 593 and706 from Table I, nos. 17, 644, 117, 429, 56, 43, 36, 49, 14, 15, 16,582, 614 and 672 from Table II, and compound no. 1 from Table VII have,when applied as 0.025 wt % spray liquors, a better fungicidal action(95%) than the prior art comparative agent A (50%).

We claim:
 1. An O-benzyloxime ether of the formula I

wherein X is N—C₁-C₄-alkoxy; Y is NR⁵; R¹, R² and R⁵ are H orC₁-C₄-alkyl; Z¹ and Z² are identical or different and each is H,halogen, methyl, methoxy or cyano; R³ is hydrogen, cyano, straight-chainor branched C₁-C₁₀-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,C_(l)-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,arylthio-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₅-haloalkenyl,C₃-C₆-cycloalkenyl, C₃-C₆-halocycloalkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₄-alkylthio, benzylthio, C₁-C₄-alkylcarbonyl,substituted or unsubstituted phenylcarbonyl, substituted orunsubstituted benzylcarbonyl, C₁-C₄-alkoxycarbonyl, substituted orunsubstituted phenoxycarbonyl, substituted or unsubstitutedbenzyloxycarbonyl, substituted or unsubstituted aryl, substituted orunsubstituted aryloxy, substituted or unsubstituted arylthio,substituted or unsubstituted aryl-C₁-C₄-alkyl, substituted orunsubstituted aryl-C₂-C₄-alkenyl, substituted or unsubstitutedaryloxy-C₁-C₄-alkyl, substituted or unsubstituted arylthio-C₁-C₄-alkyl,substituted or unsubstituted hetaryl, substituted or unsubstitutedhetaryloxy, substituted or unsubstituted hetarylthio, substituted orunsubstituted heteroaryl-C₁-C₄-alkyl, substituted or unsubstitutedhetaryl-C₂-C₄-alkenyl, substituted or unsubstitutedhetaryloxy-C₁-C₄-alkyl, substituted or unsubstituted heterocyclyl orsubstituted or unsubstituted heterocyclyloxy, halogen, N(R⁶)₂₁, wherethe radicals R⁶ are identical or different and each is H, C₁-C₆-alkyl orsubstituted or unsubstituted phenyl, —CO—N(R⁷)₂, where the radicals R⁷are identical or different and each is H or C₁-C₄-alkyl, substituted orunsubstituted meaning, in addition to hydrogen, the radicals halogen,cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl,C₁-C₄-haloalkoxy, C₁-C₁₀-alkoximino-C₁-C₂-alkyl, aryl, aryloxy,benzyloxy, hetaryl, hetaryloxy,-C₃-C₆-cycloalkyl, heterocyclyl,heterocyclyloxy; and R⁴ is substituted or unsubstituted hetaryl,substituted or unsubstituted hetaryloxy, substituted or unsubstitutedhetarylthio, substituted or unsubstituted heteroaryl-C₁-C₄-alkyl,substituted or unsubstituted hetaryl-C₂-C₄-alkenyl, substituted orunsubstituted hetaryloxy-C₁-C₄-alkyl, substituted or unsubstitutedheterocyclyl or substituted or unsubstituted heterocyclyloxy.
 2. TheO-benzyloxime ether of claim 1, wherein X=NOCH₃.
 3. The O-benzyloximeether of claim 1, wherein Y=NCH₃.
 4. The O-benzyloxime ether of claim 1,wherein both Z¹ and Z² are hydrogen.
 5. The O-benzyloxime ether of claim1, wherein R¹ is hydrogen.
 6. The O-benzyloxime ether of claim 1,wherein R² is hydrogen.
 7. The O-benzyloxime ether of claim 1, whereinR³ is methyl.
 8. The O-benzyloxime ether of claim 1, wherein R⁴ isunsubstituted or substituted hetaryl.
 9. The O-benzyloxime ether ofclaim 1, wherein R⁴ is selected from the group consisting of furanyl,thienyl, pyrrolyl, thiazolyl, triazolyl, pyridyl and pyrimidyl.
 10. TheO-benzyloxime ether of claim 1, wherein R⁴ is substituted by a radicalselected from the group consisting of halogen, phenyl, methyl, ethyl,iso-propyl, tert-butyl, methoxy, ethoxy, trifluoromethyl and2,2,2-trifluoroethoxy.
 11. The O-benzyloxime ether of claim 1, whereinR⁴ is substituted pyridyl or pyrimidyl.
 12. The O-benzyloxime ether ofclaim 1, wherein R⁴ is substituted pyrimidyl, wherein said substitutionis adjacent to a pyrimidyl-nitrogen.
 13. The O-benzyloxime ether ofclaim 1, wherein R⁴ is substituted by a radical selected from the groupconsisting of C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₂ haloalkyl, C₁₋₂ haloalkoxy,phenyl and substituted phenyl.
 14. The O-benzyloxime ether of claim 1,of the formula (II)


15. O-benzyloxime ether of the formula I

wherein X is NOCH₃; Y is NR⁵; R² is H; Z¹ is H; Z² is H, halogen,methyl, methoxy or cyano; R⁴ is pyrimidinyl, 2,6-pyrimidinyl,1,5-pyrimidinyl, 2-pyrimidinyloxy or 2-pyrimidinylthio; and R³ ishydrogen, straight-chain or branched C₁-C₁₀-alkyl, C₁-C₄-haloalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,arylthio-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₅-haloalkenyl,C₃-C₆-cycloalkenyl, C₃-C₆-halocycloalkenyl, C₂-C₆-alkenyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₄-alkylthio, benzylthio, C₁-C₄-alkylcarbonyl,substituted or unsubstituted phenylcarbonyl, substituted orunsubstituted benzylcarbonyl, C₁-C₄-alkoxycarbonyl, substituted orunsubstituted phenoxycarbonyl, substituted or unsubstitutedbenzyloxycarbonyl, substituted or unsubstituted aryl, substituted orunsubstituted aryloxy, substituted or unsubstituted arylthio,substituted or unsubstituted aryl-C₁-C₄-alkyl, substituted orunsubstituted aryl-C₂-C₄-alkenyl, or substituted or unsubstitutedaryloxy-C₁-C₄-alkyl; R⁵ is H or C₁-C₄ alkyl; and R¹ is H or C₁-C₄ alkyl.16. O-benzyloxime ether of the formula I

wherein X is NOCH₃; Y is NR⁵; R² is H; Z¹ is H; Z² is H, halogen,methyl, methoxy or cyano; R⁴ is pyridyl, 2-pyridyl, 3-pyridyl,4-pyridyl, 2-pyridyloxy, 2-pyridyl-thio, 2-pyridylmethyl,3-pyridylmethyl, 2-pyridylmethoxy, or 3′-pyridyl-2-ethenyl; and R³ ishydrogen, straight-chain or branched C₁-C₁₀-alkyl, C₁-C₄-haloalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,arylthio-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₅-haloalkenyl,C₃-C₆-cycloalkenyl, C₃-C₆-halocycloalkenyl, C₂-C₆-alkenyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₄-alkylthio, benzylthio, C₁-C₄-alkylcarbonyl,substituted or unsubstituted phenylcarbonyl, substituted orunsubstituted benzylcarbonyl, C₁-C₄-alkoxycarbonyl, substituted orunsubstituted phenoxycarbonyl, substituted or unsubstitutedbenzyloxycarbonyl, substituted or unsubstituted aryl, substituted orunsubstituted aryloxy, substituted or unsubstituted arylthio,substituted or unsubstituted aryl-C₁-C₄-alkyl, substituted orunsubstituted aryl-C₂-C₄-alkenyl, or substituted or unsubstitutedaryloxy-C₁-C₄-alkyl; R⁵ is H or C₁-C₄ alkyl; and R¹ is H or C₁-C₄ alkyl.17. A fungicide containing an inert carrier and a fungicidally effectiveamount of an O-benzyloxime ether of the formula I

wherein X is N—C₁-C₄-alkoxy; Y is NR⁵; R¹, R² and R⁵ are H orC₁-C₄-alkyl; Z¹ and Z² are identical or different and each is H,halogen, methyl, methoxy or cyano; R³ is hydrogen, cyano, straight-chainor branched C₁-C₁₀-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,C₁-C₄-alkoxy-C₁-C₄-alkyl C₁-C₄-alkylthio-C₁-C₄-alkyl,arylthio-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₅-haloalkenyl,C₃-C₆-cycloalkenyl, C₃-C₆-halocycloalkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₄-alkylthio, benzylthio, C₁-C₄-alkylcarbonyl,substituted or unsubstituted phenylcarbonyl, substituted orunsubstituted benzylcarbonyl, C₁-C₄-alkoxycarbonyl, substituted orunsubstituted phenoxycarbonyl, substituted or unsubstitutedbenzyloxycarbonyl, substituted or unsubstituted aryl, substituted orunsubstituted aryloxy, substituted or unsubstituted arylthio,substituted or unsubstituted aryl-C₁-C₄-alkyl, substituted orunsubstituted aryl-C₂-C₄-alkenyl, substituted or unsubstitutedaryloxy-C₁-C₄-alkyl, substituted or unsubstituted arylthio-C₁-C₄-alkyl,substituted or unsubstituted hetaryl, substituted or unsubstitutedhetaryloxy, substituted or unsubstituted hetarylthio, substituted orunsubstituted heteroaryl-C₁-C₄-alkyl, substituted or unsubstitutedhetaryl-C₂-C₄-alkenyl, substituted or unsubstitutedhetaryloxy-C₁-C₄-alkyl, substituted or unsubstituted heterocyclyl orsubstituted or unsubstituted heterocyclyloxy, halogen, N(R⁶)₂₁, wherethe radicals R⁶ are identical or different and each is H, C₁-C₆-alkyl orsubstituted or unsubstituted phenyl, —CO—N(R⁷)₂, where the radicals R⁷are identical or different and each is H or C₁-C₄-alkyl, substituted orunsubstituted meaning, in addition to hydrogen, the radicals halogen,cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl,C₁-C₄-haloalkoxy, C₁-C₁₀-alkoximino-C₁-C₂-alkyl, aryl, aryloxy,benzyloxy, hetaryl, hetaryloxy,-C₃-C₆-cycloalkyl, heterocyclyl,heterocyclyloxy; and R⁴ is substituted or unsubstituted hetaryl,substituted or unsubstituted hetaryloxy, substituted or unsubstitutedhetarylthio, substituted or unsubstituted heteroaryl-C₁-C₄-alkyl,substituted or unsubstituted hetaryl-C₂-C₄-alkenyl, substituted orunsubstituted hetaryloxy-C₁-C₄-alkyl, substituted or unsubstitutedheterocyclyl or substituted or unsubstituted heterocyclyloxy.